Compound, mixture thereof, material for organic electroluminescence device, organic electroluminescence device, and electronic device

ABSTRACT

Provided is a compound represented by a formula (1). In the formula (1): X 1  to X 5  each independently represent a nitrogen atom or CR 10 ; two or more of X 1  to X 5  are nitrogen atoms; Y 1  to Y 5  each independently represent a nitrogen atom or CR 20 ; one or more of Y 1  to Y 5  are nitrogen atoms; R 10 , R 20 , and R 5  to R 7  forming neither a monocyclic ring nor a fused ring, and R 8  and R 9  each independently represent a hydrogen atom, an aryl group, a heterocyclic group, or the like; a represents 0, 1, 2, or 3; b represents 0, 1, 2, or 3; and L1 and L2 each independently represent a single bond, an arylene group, a divalent heterocyclic group, or the like.

The entire disclosure of Japanese Patent Application No. 2021-005152,filed Jan. 15, 2021 is expressly incorporated by reference herein.

TECHNICAL FIELD

The present invention relates to a compound, a mixture thereof, amaterial for organic electroluminescence device, an organicelectroluminescence device, and an electronic device.

BACKGROUND ART

Upon a voltage being applied to an organic electroluminescence device(hereinafter, may be referred to as “organic EL device”), holes areinjected from an anode to an emitting layer, while electrons areinjected from a cathode to the emitting layer. The injected holes andelectrons recombine with each other in the emitting layer to formexcitons. Specifically, singlet and triplet excitons are formed atproportions of 25%:75%, respectively, due to the electron spinstatistics theorem.

Organic EL devices have been applied to full-color displays included incellular mobile phones, televisions, and the like.

There have been various studies of compounds included in organic ELdevices in order to enhance the performance of the organic EL devices(e.g., see Document 1: International Publication No. WO 2019/163959,Document 2: International Publication No. WO 2018/173882, Document 3:International Publication No. WO 99/19419, Document 4: U.S. PatentApplication Publication No. 2007/051944, Document 5: KR 10-2006-0122874A, and Document 6: Japanese Unexamined Patent Application PublicationNo. 2007-520875).

Examples of the performance of an organic EL device include luminance,emission wavelength, chromaticity, luminous efficiency, drive voltage,and lifetime.

SUMMARY OF THE INVENTION

An object of the invention is to provide a compound capable of enhancingthe performance of an organic EL device, a mixture thereof capable ofenhancing the performance of an organic EL device, a material fororganic electroluminescence device including the compound or mixture, anorganic electroluminescence device including the compound or mixture,and an electronic device including the organic electroluminescencedevice.

According to an aspect of the invention, there is provided a compoundrepresented by a formula (1) below.

In the formula (1),

X¹ to X⁵ each independently represent a nitrogen atom or CR¹⁰,

two or more of X¹ to X⁵ are nitrogen atoms, and

at least one combination of adjacent two or more of a plurality of R¹⁰are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

Y¹ to Y⁵ each independently represent a nitrogen atom or CR²⁰ ,

one or more of Y¹ to Y⁵ are nitrogen atoms,

at least one combination of adjacent two or more of a plurality of R²⁰are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

at least one combination of adjacent two or more of a plurality of R⁵are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

at least one combination of adjacent two or more of a plurality of R⁶are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

at least one combination of adjacent two or more of a plurality of R⁷are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

R¹⁰, R²⁰, and R⁵ to R⁷ forming neither the substituted or unsubstitutedmonocyclic ring nor the substituted or unsubstituted fused ring, and R⁸and R⁹ each independently represent a hydrogen atom, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted alkenylgroup having 2 to 50 carbon atoms, a substituted or unsubstitutedalkynyl group having 2 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a grouprepresented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a group represented by —O—(R₉₀₄),a group represented by —S—(R₉₀₅), a group represented by —N(R₉₀₆)(R₉₀₇),a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to50 ring atoms,

when a plurality of R¹⁰ are present, the plurality of R¹⁰ are mutuallythe same or different,

when a plurality of R²⁰ are present, the plurality of R²⁰ are mutuallythe same or different,

the plurality of R⁵ are mutually the same or different,

the plurality of R⁶ are mutually the same or different,

the plurality of R⁷ are mutually the same or different,

a represents 0, 1, 2, or 3,

when a is 2 or 3, a plurality of L1 are mutually the same or different,

b represents 0, 1, 2, or 3,

when b is 2 or 3, a plurality of L2 are mutually the same or different,

when a and b are each independently 1, 2, or 3,

L1 and L2 each independently represent a single bond, a substituted orunsubstituted arylene group having 6 to 50 ring carbon atoms, or asubstituted or unsubstituted divalent heterocyclic group having 5 to 50ring atoms,

when only one of Y¹ to Y⁵ is a nitrogen atom, L2 is not a single bond,or any of Y¹ to Y⁵ other than a nitrogen atom is not CH.

In the compound represented by the formula (1),

R₉₀₁ to R₉₀₇ each independently represent a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to50 ring atoms,

when two or more R₉₀₁ are present, the two or more R₉₀₁ are mutually thesame or different; when two or more R₉₀₂ are present, the two or moreR₉₀₂ are mutually the same or different; when two or more R₉₀₃ arepresent, the two or more R₉₀₃ are mutually the same or different; whentwo or more R₉₀₄ are present, the two or more R₉₀₄ are mutually the sameor different; when two or more R₉₀₅ are present, the two or more R₉₀₅are mutually the same or different; when two or more R₉₀₆ are present,the two or more R₉₀₆ are mutually the same or different; and when two ormore R₉₀₇ are present, the two or more R₉₀₇ are mutually the same ordifferent.

According to an aspect of the invention, there is provided a mixtureincluding the compound according to the above aspect of the invention asa first compound; and a second compound that is an enantiomer of thefirst compound.

According to an aspect of the invention, there is provided a materialfor organic electroluminescence device including the compound accordingto the above aspect of the invention.

According to an aspect of the invention, there is provided a materialfor organic electroluminescence device including the mixture accordingto the above aspect of the invention.

According to an aspect of the invention, there is provided an organicelectroluminescence device including: a cathode; an anode; and one ormore organic layers interposed between the cathode and the anode, inwhich at least one of the organic layers includes the compound accordingto the above aspect of the invention as a first compound.

According to an aspect of the invention, there is provided an electronicdevice including the organic electroluminescence device according to theabove aspect of the invention.

According to an aspect of the invention, there can be provided acompound capable of enhancing the performance of an organic EL device, amixture thereof capable of enhancing the performance of an organic ELdevice, a material for organic electroluminescence device including thecompound or mixture, an organic electroluminescence device including thecompound or mixture, and an electronic device including the organicelectroluminescence device.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic diagram of an exemplary layer arrangement of anorganic EL device according to an aspect of the invention.

FIG. 2 is a schematic diagram of another exemplary layer arrangement ofan organic EL device according to an aspect of the invention.

DESCRIPTION OF EMBODIMENT(S) Definitions

Herein, a hydrogen atom includes isotope having different numbers ofneutrons, specifically, protium, deuterium and tritium.

In chemical formulae herein, it is assumed that a hydrogen atom (i.e.protium, deuterium or tritium) is bonded to each of bondable positionsthat are not annexed with signs “R” or the like or “D” representing adeuterium.

Herein, the ring carbon atoms refer to the number of carbon atoms amongatoms forming a ring of a compound (e.g., a monocyclic compound,fused-ring compound, cross-linking compound, carbon ring compound, andheterocyclic compound) in which the atoms are bonded to each other toform the ring. When the ring is substituted by a substituent(s), carbonatom(s) contained in the substituent(s) is not counted in the ringcarbon atoms. Unless otherwise specified, the same applies to the “ringcarbon atoms” described later. For instance, a benzene ring has 6 ringcarbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridinering has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms.Further, for instance, 9,9-diphenylfluorenyl group has 13 ring carbonatoms and 9,9′-spirobifluorenyl group has 25 ring carbon atoms.

When a benzene ring is substituted by a substituent in a form of, forinstance, an alkyl group, the number of carbon atoms of the alkyl groupis not counted in the number of the ring carbon atoms of the benzenering. Accordingly, the benzene ring substituted by an alkyl group has 6ring carbon atoms. When a naphthalene ring is substituted by asubstituent in a form of, for instance, an alkyl group, the number ofcarbon atoms of the alkyl group is not counted in the number of the ringcarbon atoms of the naphthalene ring. Accordingly, the naphthalene ringsubstituted by an alkyl group has 10 ring carbon atoms.

Herein, the ring atoms refer to the number of atoms forming a ring of acompound (e.g., a monocyclic compound, fused-ring compound,cross-linking compound, carbon ring compound, and heterocyclic compound)in which the atoms are bonded to each other to form the ring (e.g.,monocyclic ring, fused ring, and ring assembly). Atom(s) not forming thering (e.g., hydrogen atom(s) for saturating the valence of the atomwhich forms the ring) and atom(s) in a substituent by which the ring issubstituted are not counted as the ring atoms. Unless otherwisespecified, the same applies to the “ring atoms” described later. Forinstance, a pyridine ring has 6 ring atoms, a quinazoline ring has 10ring atoms, and a furan ring has 5 ring atoms. For instance, the numberof hydrogen atom(s) bonded to a pyridine ring or the number of atomsforming a substituent are not counted as the pyridine ring atoms.Accordingly, a pyridine ring bonded to a hydrogen atom(s) or asubstituent(s) has 6 ring atoms. For instance, the hydrogen atom(s)bonded to carbon atom(s) of a quinazoline ring or the atoms forming asubstituent are not counted as the quinazoline ring atoms. Accordingly,a quinazoline ring bonded to hydrogen atom(s) or a substituent(s) has 10ring atoms.

Herein, “XX to YY carbon atoms” in the description of “substituted orunsubstituted ZZ group having XX to YY carbon atoms” represent carbonatoms of an unsubstituted ZZ group and do not include carbon atoms of asubstituent(s) of the substituted ZZ group. Herein, “YY” is larger than“XX,” “XX” representing an integer of 1 or more and “YY” representing aninteger of 2 or more.

Herein, “XX to YY atoms” in the description of “substituted orunsubstituted ZZ group having XX to YY atoms” represent atoms of anunsubstituted ZZ group and do not include atoms of a substituent(s) ofthe substituted ZZ group. Herein, “YY” is larger than “XX,” “XX”representing an integer of 1 or more and “YY” representing an integer of2 or more.

Herein, an unsubstituted ZZ group refers to an “unsubstituted ZZ group”in a “substituted or unsubstituted ZZ group,” and a substituted ZZ grouprefers to a “substituted ZZ group” in a “substituted or unsubstituted ZZgroup.”

Herein, the term “unsubstituted” used in a “substituted or unsubstitutedZZ group” means that a hydrogen atom(s) in the ZZ group is notsubstituted with a substituent(s). The hydrogen atom(s) in the“unsubstituted ZZ group” is protium, deuterium, or tritium.

Herein, the term “substituted” used in a “substituted or unsubstitutedZZ group” means that at least one hydrogen atom in the ZZ group issubstituted with a substituent. Similarly, the term “substituted” usedin a “BB group substituted by AA group” means that at least one hydrogenatom in the BB group is substituted with the AA group.

Substituents Mentioned Herein

Substituents mentioned herein will be described below.

An “unsubstituted aryl group” mentioned herein has, unless otherwisespecified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18ring carbon atoms.

An “unsubstituted heterocyclic group” mentioned herein has, unlessotherwise specified herein, 5 to 50, preferably 5 to 30, more preferably5 to 18 ring atoms.

An “unsubstituted alkyl group” mentioned herein has, unless otherwisespecified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6carbon atoms.

An “unsubstituted alkenyl group” mentioned herein has, unless otherwisespecified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6carbon atoms.

An “unsubstituted alkynyl group” mentioned herein has, unless otherwisespecified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6carbon atoms.

An “unsubstituted cycloalkyl group” mentioned herein has, unlessotherwise specified herein, 3 to 50, preferably 3 to 20, more preferably3 to 6 ring carbon atoms.

An “unsubstituted arylene group” mentioned herein has, unless otherwisespecified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18ring carbon atoms.

An “unsubstituted divalent heterocyclic group” mentioned herein has,unless otherwise specified herein, 5 to 50, preferably 5 to 30, morepreferably 5 to 18 ring atoms.

An “unsubstituted alkylene group” mentioned herein has, unless otherwisespecified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6carbon atoms.

Substituted or Unsubstituted Aryl Group

Specific examples (specific example group G1) of the “substituted orunsubstituted aryl group” mentioned herein include unsubstituted arylgroups (specific example group G1A) below and substituted aryl groups(specific example group G1B) below. (Herein, an unsubstituted aryl grouprefers to an “unsubstituted aryl group” in a “substituted orunsubstituted aryl group”, and a substituted aryl group refers to a“substituted aryl group” in a “substituted or unsubstituted arylgroup.”) A simply termed “aryl group” herein includes both of an“unsubstituted aryl group” and a “substituted aryl group.”

The “substituted aryl group” refers to a group derived by substitutingat least one hydrogen atom in an “unsubstituted aryl group” with asubstituent. Examples of the “substituted aryl group” include a groupderived by substituting at least one hydrogen atom in the “unsubstitutedaryl group” in the specific example group G1A below with a substituent,and examples of the substituted aryl group in the specific example groupG1B below. It should be noted that the examples of the “unsubstitutedaryl group” and the “substituted aryl group” mentioned herein are merelyexemplary, and the “substituted aryl group” mentioned herein includes agroup derived by further substituting a hydrogen atom bonded to a carbonatom of a skeleton of a “substituted aryl group” in the specific examplegroup G1B below, and a group derived by further substituting a hydrogenatom of a substituent of the “substituted aryl group” in the specificexample group G1B below.

Unsubstituted Aryl Group (Specific Example Group G1A):

phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group,1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group,phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenylgroup, chrysenyl group, benzochrysenyl group, triphenylenyl group,benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenylgroup, 9,9′-spirobifluorenyl group, benzofluorenyl group,dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group,perylenyl group, and a monovalent aryl group derived by removing onehydrogen atom from cyclic structures represented by formulae (TEMP-1) to(TEMP-15) below.

Substituted Aryl Group (Specific Example Group G1B):

o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group,meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group,meta-isopropylphenyl group, ortho-isopropylphenyl group,para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenylgroup, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group,9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group,9,9-bis(4-isopropylphenyl)fluorenyl group,9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group,triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthylgroup, naphthylphenyl group, and a group derived by substituting atleast one hydrogen atom of a monovalent group derived from one of thecyclic structures represented by the formulae (TEMP-1) to (TEMP-15) witha substituent.

Substituted or Unsubstituted Heterocyclic Group

The “heterocyclic group” mentioned herein refers to a cyclic grouphaving at least one hetero atom in the ring atoms. Specific examples ofthe hetero atom include a nitrogen atom, oxygen atom, sulfur atom,silicon atom, phosphorus atom, and boron atom.

The “heterocyclic group” mentioned herein is a monocyclic group or afused-ring group.

The “heterocyclic group” mentioned herein is an aromatic heterocyclicgroup or a non-aromatic heterocyclic group.

Specific examples (specific example group G2) of the “substituted orunsubstituted heterocyclic group” mentioned herein include unsubstitutedheterocyclic groups (specific example group G2A) and substitutedheterocyclic groups (specific example group G2B). (Herein, anunsubstituted heterocyclic group refers to an “unsubstitutedheterocyclic group” in a “substituted or unsubstituted heterocyclicgroup,” and a substituted heterocyclic group refers to a “substitutedheterocyclic group” in a “substituted or unsubstituted heterocyclicgroup.”) A simply termed “heterocyclic group” herein includes both of“unsubstituted heterocyclic group” and “substituted heterocyclic group.”

The “substituted heterocyclic group” refers to a group derived bysubstituting at least one hydrogen atom in an “unsubstitutedheterocyclic group” with a substituent. Specific examples of the“substituted heterocyclic group” include a group derived by substitutingat least one hydrogen atom in the “unsubstituted heterocyclic group” inthe specific example group G2A below with a substituent, and examples ofthe substituted heterocyclic group in the specific example group G2Bbelow. It should be noted that the examples of the “unsubstitutedheterocyclic group” and the “substituted heterocyclic group” mentionedherein are merely exemplary, and the “substituted heterocyclic group”mentioned herein includes a group derived by further substituting ahydrogen atom bonded to a ring atom of a skeleton of a “substitutedheterocyclic group” in the specific example group G2B below, and a groupderived by further substituting a hydrogen atom of a substituent of the“substituted heterocyclic group” in the specific example group G2Bbelow.

The specific example group G2A includes, for instance, unsubstitutedheterocyclic groups including a nitrogen atom (specific example groupG2A1) below, unsubstituted heterocyclic groups including an oxygen atom(specific example group G2A2) below, unsubstituted heterocyclic groupsincluding a sulfur atom (specific example group G2A3) below, andmonovalent heterocyclic groups (specific example group G2A4) derived byremoving a hydrogen atom from cyclic structures represented by formulae(TEMP-16) to (TEMP-33) below.

The specific example group G2B includes, for instance, substitutedheterocyclic groups including a nitrogen atom (specific example groupG2B1) below, substituted heterocyclic groups including an oxygen atom(specific example group G2B2) below, substituted heterocyclic groupsincluding a sulfur atom (specific example group G2B3) below, and groupsderived by substituting at least one hydrogen atom of the monovalentheterocyclic groups (specific example group G2B4) derived from thecyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.

Unsubstituted Heterocyclic Groups Including Nitrogen Atom (SpecificExample Group G2A1):

pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group,tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group,thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group,pyridazynyl group, pyrimidinyl group, pyrazinyl group, triazinyl group,indolyl group, isoindolyl group, indolizinyl group, quinolizinyl group,quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group,quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolylgroup, phenanthrolinyl group, phenanthridinyl group, acridinyl group,phenazinyl group, carbazolyl group, benzocarbazolyl group, morpholinogroup, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group,and diazacarbazolyl group.

Unsubstituted Heterocyclic Groups Including Oxygen Atom (SpecificExample Group G2A2):

furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group,xanthenyl group, benzofuranyl group, isobenzofuranyl group,dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group,benzisoxazolyl group, phenoxazinyl group, morpholino group,dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranylgroup, azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.

Unsubstituted Heterocyclic Groups Including Sulfur Atom (SpecificExample Group G2A3):

thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group,benzothiophenyl group (benzothienyl group), isobenzothiophenyl group(isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group),naphthobenzothiophenyl group (nahthobenzothienyl group), benzothiazolylgroup, benzisothiazolyl group, phenothiazinyl group, dinaphthothiophenylgroup (dinaphthothienyl group), azadibenzothiophenyl group(azadibenzothienyl group), diazadibenzothiophenyl group(diazadibenzothienyl group), azanaphthobenzothiophenyl group(azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group(diazanaphthobenzothienyl group).

Monovalent Heterocyclic Groups Derived by Removing One Hydrogen Atomfrom Cyclic Structures Represented by formulae (TEMP-16) to (TEMP-33)(Specific Example Group G2A4):

In the formulae (TEMP-16) to (TEMP-33), X_(A) and Y_(A) are eachindependently an oxygen atom, a sulfur atom, NH, or CH₂, with a provisothat at least one of X_(A) or Y_(A) is an oxygen atom, a sulfur atom, orNH.

When at least one of X_(A) or Y_(A) in the formulae (TEMP-16) to(TEMP-33) is NH or CH₂, the monovalent heterocyclic groups derived fromthe cyclic structures represented by the formulae (TEMP-16) to (TEMP-33)include a monovalent group derived by removing one hydrogen atom from NHor CH₂.

Substituted Heterocyclic Groups Including Nitrogen Atom (SpecificExample Group G2B1):

(9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group,(9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group,diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group,methylbenzimidazolyl group, ethylbenzimidazolyl group phenyltriazinylgroup, biphenylyltriazinyl group, diphenyltriazinyl group,phenylquinazolinyl group, and biphenylquinazolinyl group.

Substituted Heterocyclic Groups Including Oxygen Atom (Specific ExampleGroup G2B2):

phenyldibenzofuranyl group, methyldibenzofuranyl group,t-butyldibenzofuranyl group, and monovalent residue ofspiro[9H-xanthene-9,9′-[9H]fluorene].

Substituted Heterocyclic Groups Including Sulfur Atom (Specific ExampleGroup G2B3):

phenyldibenzothiophenyl group, methyldibenzothiophenyl group,

t-butyldibenzothiophenyl group, and monovalent residue ofspiro[9H-thioxanthene-9,9′-[9H]fluorene].

Groups Obtained by Substituting at Least One Hydrogen Atom of MonovalentHeterocyclic Group Derived from Cyclic Structures Represented byFormulae (TEMP-16) to (TEMP-33) with Substituent (Specific Example GroupG2B4):

The “at least one hydrogen atom of a monovalent heterocyclic group”means at least one hydrogen atom selected from a hydrogen atom bonded toa ring carbon atom of the monovalent heterocyclic group, a hydrogen atombonded to a nitrogen atom of at least one of XA or YA in a form of NH,and a hydrogen atom of one of XA and YA in a form of a methylene group(CH2).

Substituted or Unsubstituted Alkyl Group

Specific examples (specific example group G3) of the “substituted orunsubstituted alkyl group” mentioned herein include unsubstituted alkylgroups (specific example group G3A) and substituted alkyl groups(specific example group G3B) below. (Herein, an unsubstituted alkylgroup refers to an “unsubstituted alkyl group” in a “substituted orunsubstituted alkyl group,” and a substituted alkyl group refers to a“substituted alkyl group” in a “substituted or unsubstituted alkylgroup.”) A simply termed “alkyl group” herein includes both of“unsubstituted alkyl group” and “substituted alkyl group.”

The “substituted alkyl group” refers to a group derived by substitutingat least one hydrogen atom in an “unsubstituted alkyl group” with asubstituent. Specific examples of the “substituted alkyl group” includea group derived by substituting at least one hydrogen atom of an“unsubstituted alkyl group” (specific example group G3A) below with asubstituent, and examples of the substituted alkyl group (specificexample group G3B) below. Herein, the alkyl group for the “unsubstitutedalkyl group” refers to a chain alkyl group. Accordingly, the“unsubstituted alkyl group” include linear “unsubstituted alkyl group”and branched “unsubstituted alkyl group.” It should be noted that theexamples of the “unsubstituted alkyl group” and the “substituted alkylgroup” mentioned herein are merely exemplary, and the “substituted alkylgroup” mentioned herein includes a group derived by further substitutinga hydrogen atom of a skeleton of the “substituted alkyl group” in thespecific example group G3B, and a group derived by further substitutinga hydrogen atom of a substituent of the “substituted alkyl group” in thespecific example group G3B.

Unsubstituted Alkyl Group (Specific Example Group G3A):

methyl group, ethyl group, n-propyl group, isopropyl group, n-butylgroup,

isobutyl group, s-butyl group, and t-butyl group.

Substituted Alkyl Group (Specific Example Group G3B):

heptafluoropropyl group (including isomer thereof), pentafluoroethylgroup,

2,2,2-trifluoroethyl group, and trifluoromethyl group.

Substituted or Unsubstituted Alkenyl Group

Specific examples (specific example group G4) of the “substituted orunsubstituted alkenyl group” mentioned herein include unsubstitutedalkenyl groups (specific example group G4A) and substituted alkenylgroups (specific example group G4B). (Herein, an unsubstituted alkenylgroup refers to an “unsubstituted alkenyl group” in a “substituted orunsubstituted alkenyl group,” and a substituted alkenyl group refers toa “substituted alkenyl group” in a “substituted or unsubstituted alkenylgroup.”) A simply termed “alkenyl group” herein includes both of“unsubstituted alkenyl group” and “substituted alkenyl group.”

The “substituted alkenyl group” refers to a group derived bysubstituting at least one hydrogen atom in an “unsubstituted alkenylgroup” with a substituent. Specific examples of the “substituted alkenylgroup” include an “unsubstituted alkenyl group” (specific example groupG4A) substituted by a substituent, and examples of the substitutedalkenyl group (specific example group G4B) below. It should be notedthat the examples of the “unsubstituted alkenyl group” and the“substituted alkenyl group” mentioned herein are merely exemplary, andthe “substituted alkenyl group” mentioned herein includes a groupderived by further substituting a hydrogen atom of a skeleton of the“substituted alkenyl group” in the specific example group G4B with asubstituent, and a group derived by further substituting a hydrogen atomof a substituent of the “substituted alkenyl group” in the specificexample group G4B with a substituent.

Unsubstituted Alkenyl Group (Specific Example Group G4A):

vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and3-butenyl group.

Substituted Alkenyl Group (Specific Example Group G4B):

1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group,1,1-dimethylallyl group, 2-methylallyl group, and1,2-dimethylallylgroup.

Substituted or Unsubstituted Alkynyl Group

Specific examples (specific example group G5) of the “substituted orunsubstituted alkynyl group” mentioned herein include unsubstitutedalkynyl groups (specific example group G5A) below. (Herein, anunsubstituted alkynyl group refers to an “unsubstituted alkynyl group”in a “substituted or unsubstituted alkynyl group.”) A simply termed“alkynyl group” herein includes both of “unsubstituted alkynyl group”and “substituted alkynyl group.”

The “substituted alkynyl group” refers to a group derived bysubstituting at least one hydrogen atom in an “unsubstituted alkynylgroup” with a substituent. Specific examples of the “substituted alkynylgroup” include a group derived by substituting at least one hydrogenatom of the “unsubstituted alkynyl group” (specific example group G5A)below with a substituent.

Unsubstituted Alkynyl Group (Specific Example Group G5A):

ethynyl group.

Substituted or Unsubstituted Cycloalkyl Group

Specific examples (specific example group G6) of the “substituted orunsubstituted cycloalkyl group” mentioned herein include unsubstitutedcycloalkyl groups (specific example group G6A) and substitutedcycloalkyl groups (specific example group G6B). (Herein, anunsubstituted cycloalkyl group refers to an “unsubstituted cycloalkylgroup” in a “substituted or unsubstituted cycloalkyl group,” and asubstituted cycloalkyl group refers to a “substituted cycloalkyl group”in a “substituted or unsubstituted cycloalkyl group.”) A simply termed“cycloalkyl group” herein includes both of “unsubstituted cycloalkylgroup” and “substituted cycloalkyl group.”

The “substituted cycloalkyl group” refers to a group derived bysubstituting at least one hydrogen atom of an “unsubstituted cycloalkylgroup” with a substituent. Specific examples of the “substitutedcycloalkyl group” include a group derived by substituting at least onehydrogen atom of the “unsubstituted cycloalkyl group” (specific examplegroup G6A) below with a substituent, and examples of the substitutedcycloalkyl group (specific example group G6B) below. It should be notedthat the examples of the “unsubstituted cycloalkyl group” and the“substituted cycloalkyl group” mentioned herein are merely exemplary,and the “substituted cycloalkyl group” mentioned herein includes a groupderived by substituting at least one hydrogen atom bonded to a carbonatom of a skeleton of the “substituted cycloalkyl group” in the specificexample group G6B with a substituent, and a group derived by furthersubstituting a hydrogen atom of a substituent of the “substitutedcycloalkyl group” in the specific example group G6B with a substituent.Unsubstituted Cycloalkyl Group (Specific Example Group G6A):

cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexylgroup, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and2-norbornyl group.

Substituted Cycloalkyl Group (Specific Example Group G6B):

4-methylcyclohexyl group.

Group Represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃)

Specific examples (specific example group G7) of the group representedherein by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃) include: —Si(G1)(G1)(G1);—Si(G1)(G2)(G2); —Si(G1)(G1)(G2); —Si(G2)(G2)(G2); —Si(G3)(G3)(G3); and—Si(G6)(G6)(G6),

where

G1 represents a “substituted or unsubstituted aryl group” in thespecific example group G1;

G2 represents a “substituted or unsubstituted heterocyclic group” in thespecific example group G2;

G3 represents a “substituted or unsubstituted alkyl group” in thespecific example group G3;

G6 represents a “substituted or unsubstituted cycloalkyl group” in thespecific example group G6;

a plurality of G1 in —Si(G1)(G1)(G1) are mutually the same or different;

a plurality of G2 in —Si(G1)(G2)(G2) are mutually the same or different;

a plurality of G1 in —Si(G1)(G1)(G2) are mutually the same or different;

a plurality of G2 in —Si(G2)(G2)(G2) are mutually the same or different;

a plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different;and

a plurality of G6 in —Si(G6)(G6)(G6) are mutually the same or different.

Group Represented by —O—(R₉₀₄)

Specific examples (specific example group G8) of a group represented by—O—(R₉₀₄) herein include: —O(G1); —O(G2); —O(G3); and —O(G6),

where:

G1 represents a “substituted or unsubstituted aryl group” in thespecific example group G1;

G2 represents a “substituted or unsubstituted heterocyclic group” in thespecific example group G2;

G3 represents a “substituted or unsubstituted alkyl group” in thespecific example group G3; and

G6 represents a “substituted or unsubstituted cycloalkyl group” in thespecific example group G6.

Group Represented by —S—(R₉₀₅)

Specific examples (specific example group G9) of a group representedherein by —S—(R₉₀₅) include: —S(G1); —S(G2); —S(G3); and —S(G6),

where:

G1 represents a “substituted or unsubstituted aryl group” in thespecific example group G1;

G2 represents a “substituted or unsubstituted heterocyclic group” in thespecific example group G2;

G3 represents a “substituted or unsubstituted alkyl group” in thespecific example group G3; and

G6 represents a “substituted or unsubstituted cycloalkyl group” in thespecific example group G6.

Group Represented by —N(R₉₀₆)(R₉₀₇)

Specific examples (specific example group G10) of a group representedherein by —N(R₉₀₆)(R₉₀₇) include: —N(G1)(G1); —N(G2)(G2); —N(G1)(G2);—N(G3)(G3); and —N(G6)(G6),

where:

G1 represents a “substituted or unsubstituted aryl group” in thespecific example group G1;

G2 represents a “substituted or unsubstituted heterocyclic group” in thespecific example group G2;

G3 represents a “substituted or unsubstituted alkyl group” in thespecific example group G3;

G6 represents a “substituted or unsubstituted cycloalkyl group” in thespecific example group G6;

a plurality of G1 in —N(G1)(G1) are mutually the same or different;

a plurality of G2 in —N(G2)(G2) are mutually the same or different;

a plurality of G3 in —N(G3)(G3) are mutually the same or different; and

a plurality of G6 in —N(G6)(G6) are mutually the same or different.

Halogen Atom

Specific examples (specific example group G11) of “halogen atom”mentioned herein include a fluorine atom, chlorine atom, bromine atom,and iodine atom.

Substituted or Unsubstituted Fluoroalkyl Group

The “substituted or unsubstituted fluoroalkyl group” mentioned hereinrefers to a group derived by substituting at least one hydrogen atombonded to at least one of carbon atoms forming an alkyl group in the“substituted or unsubstituted alkyl group” with a fluorine atom, andalso includes a group (perfluoro group) derived by substituting all ofhydrogen atoms bonded to carbon atoms forming the alkyl group in the“substituted or unsubstituted alkyl group” with fluorine atoms. An“unsubstituted fluoroalkyl group” has, unless otherwise specifiedherein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbonatoms. The “substituted fluoroalkyl group” refers to a group derived bysubstituting at least one hydrogen atom in a “fluoroalkyl group” with asubstituent. It should be noted that the examples of the “substitutedfluoroalkyl group” mentioned herein include a group derived by furthersubstituting at least one hydrogen atom bonded to a carbon atom of analkyl chain of a “substituted fluoroalkyl group” with a substituent, anda group derived by further substituting at least one hydrogen atom of asubstituent of the “substituted fluoroalkyl group” with a substituent.Specific examples of the “substituted fluoroalkyl group” include a groupderived by substituting at least one hydrogen atom of the “alkyl group”(specific example group G3) with a fluorine atom.

Substituted or Unsubstituted Haloalkyl Group

The “substituted or unsubstituted haloalkyl group” mentioned hereinrefers to a group derived by substituting at least one hydrogen atombonded to carbon atoms forming the alkyl group in the “substituted orunsubstituted alkyl group” with a halogen atom, and also includes agroup derived by substituting all hydrogen atoms bonded to carbon atomsforming the alkyl group in the “substituted or unsubstituted alkylgroup” with halogen atoms. An “unsubstituted haloalkyl group” has,unless otherwise specified herein, 1 to 50, preferably 1 to 30, morepreferably 1 to 18 carbon atoms. The “substituted haloalkyl group”refers to a group derived by substituting at least one hydrogen atom ina “haloalkyl group” with a substituent. It should be noted that theexamples of the “substituted haloalkyl group” mentioned herein include agroup derived by further substituting at least one hydrogen atom bondedto a carbon atom of an alkyl chain of a “substituted haloalkyl group”with a substituent, and a group derived by further substituting at leastone hydrogen atom of a substituent of the “substituted haloalkyl group”with a substituent. Specific examples of the “unsubstituted haloalkylgroup” include a group derived by substituting at least one hydrogenatom of the “alkyl group” (specific example group G3) with a halogenatom. The haloalkyl group is sometimes referred to as a halogenatedalkyl group.

Substituted or Unsubstituted Alkoxy Group

Specific examples of a “substituted or unsubstituted alkoxy group”mentioned herein include a group represented by —O(G3), G3 being the“substituted or unsubstituted alkyl group” in the specific example groupG3. An “unsubstituted alkoxy group” has, unless otherwise specifiedherein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbonatoms.

Substituted or Unsubstituted Alkylthio Group

Specific examples of a “substituted or unsubstituted alkylthio group”mentioned herein include a group represented by —S(G3), G3 being the“substituted or unsubstituted alkyl group” in the specific example groupG3. An “unsubstituted alkylthio group” has, unless otherwise specifiedherein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbonatoms.

Substituted or Unsubstituted Aryloxy Group

Specific examples of a “substituted or unsubstituted aryloxy group”mentioned herein include a group represented by —O(G1), G1 being the“substituted or unsubstituted aryl group” in the specific example groupG1. An “unsubstituted aryloxy group” has, unless otherwise specifiedherein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbonatoms.

Substituted or Unsubstituted Arylthio Group

Specific examples of a “substituted or unsubstituted arylthio group”mentioned herein include a group represented by —S(G1), G1 being the“substituted or unsubstituted aryl group” in the specific example groupG1. An “unsubstituted arylthio group” has, unless otherwise specifiedherein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbonatoms.

Substituted or Unsubstituted Trialkylsilyl Group

Specific examples of a “trialkylsilyl group” mentioned herein include agroup represented by —Si(G3)(G3)(G3), G3 being the “substituted orunsubstituted alkyl group” in the specific example group G3. Theplurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different.Each of the alkyl groups in the “trialkylsilyl group” has, unlessotherwise specified herein, 1 to 50, preferably 1 to 20, more preferably1 to 6 carbon atoms.

Substituted or Unsubstituted Aralkyl Group

Specific examples of a “substituted or unsubstituted aralkyl group”mentioned herein include a group represented by (G3)-(G1), G3 being the“substituted or unsubstituted alkyl group” in the specific example groupG3, G1 being the “substituted or unsubstituted aryl group” in thespecific example group G1. Accordingly, the “aralkyl group” is a groupderived by substituting a hydrogen atom of the “alkyl group” with asubstituent in a form of the “aryl group,” which is an example of the“substituted alkyl group.” An “unsubstituted aralkyl group,” which is an“unsubstituted alkyl group” substituted by an “unsubstituted arylgroup,” has, unless otherwise specified herein, 7 to 50 carbon atoms,preferably 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms.

Specific examples of the “substituted or unsubstituted aralkyl group”include a benzyl group, 1-phenylethyl group, 2-phenylethyl group,1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group,a-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethylgroup, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group,β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethylgroup, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

Preferable examples of the substituted or unsubstituted aryl groupmentioned herein include, unless otherwise specified herein, a phenylgroup, p-biphenyl group, m-biphenyl group, o-biphenyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group,1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group,pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group,9,9′-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and9,9-diphenylfluorenyl group.

Preferable examples of the substituted or unsubstituted heterocyclicgroup mentioned herein include, unless otherwise specified herein, apyridyl group, pyrimidinyl group, triazinyl group, quinolyl group,isoquinolyl group, quinazolinyl group, benzimidazolyl group,phenanthrolinyl group, carbazolyl group (1-carbazolyl group,2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group,diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group,azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenylgroup, naphthobenzothiophenyl group, azadibenzothiophenyl group,diazadibenzothiophenyl group, (9-phenyl)carbazolyl group((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group,(9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group),(9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group,diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group,phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinylgroup, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

The carbazolyl group mentioned herein is, unless otherwise specifiedherein, specifically a group represented by one of formulae below.

The (9-phenyl)carbazolyl group mentioned herein is, unless otherwisespecified herein, specifically a group represented by one of formulaebelow.

In the formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bondingposition.

The dibenzofuranyl group and dibenzothiophenyl group mentioned hereinare, unless otherwise specified herein, each specifically represented byone of formulae below.

In the formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

Preferable examples of the substituted or unsubstituted alkyl groupmentioned herein include, unless otherwise specified herein, a methylgroup, ethyl group, propyl group, isopropyl group, n-butyl group,isobutyl group, and t-butyl group.

Substituted or Unsubstituted Arylene Group

The “substituted or unsubstituted arylene group” mentioned herein is,unless otherwise specified herein, a divalent group derived by removingone hydrogen atom on an aryl ring of the “substituted or unsubstitutedaryl group.” Specific examples of the “substituted or unsubstitutedarylene group” (specific example group G12) include a divalent groupderived by removing one hydrogen atom on an aryl ring of the“substituted or unsubstituted aryl group” in the specific example groupG1.

Substituted or Unsubstituted Divalent Heterocyclic Group

The “substituted or unsubstituted divalent heterocyclic group” mentionedherein is, unless otherwise specified herein, a divalent group derivedby removing one hydrogen atom on a heterocycle of the “substituted orunsubstituted heterocyclic group.” Specific examples of the “substitutedor unsubstituted divalent heterocyclic group” (specific example groupG13) include a divalent group derived by removing one hydrogen atom on aheterocyclic ring of the “substituted or unsubstituted heterocyclicgroup” in the specific example group G2.

Substituted or Unsubstituted Alkylene Group

The “substituted or unsubstituted alkylene group” mentioned herein is,unless otherwise specified herein, a divalent group derived by removingone hydrogen atom on an alkyl chain of the “substituted or unsubstitutedalkyl group.” Specific examples of the “substituted or unsubstitutedalkylene group” (specific example group G14) include a divalent groupderived by removing one hydrogen atom on an alkyl chain of the“substituted or unsubstituted alkyl group” in the specific example groupG3.

The substituted or unsubstituted arylene group mentioned herein is,unless otherwise specified herein, preferably any one of groupsrepresented by formulae (TEMP-42) to (TEMP-68) below.

In the formulae (TEMP-42) to (TEMP-52), Q₁ to Q₁₀ are each independentlya hydrogen atom or a substituent.

In the formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

In the formulae (TEMP-53) to (TEMP-62), Q₁ to Q₁₀ are each independentlya hydrogen atom or a substituent.

In the formulae, Q₉ and Q₁₀ may be mutually bonded through a single bondto form a ring.

In the formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

In the formulae (TEMP-63) to (TEMP-68), Q₁ to Q₈ are each independentlya hydrogen atom or a substituent.

In the formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

The substituted or unsubstituted divalent heterocyclic group mentionedherein is, unless otherwise specified herein, preferably a grouprepresented by any one of formulae (TEMP-69) to (TEMP-102) below.

In the formulae (TEMP-69) to (TEMP-82), Q₁ to Q₉ are each independentlya hydrogen atom or a substituent.

In the formulae (TEMP-83) to (TEMP-102), Q₁ to Q₈ are each independentlya hydrogen atom or a substituent.

The substituent mentioned herein has been described above. Instance of“Bonded to Form Ring”

Instances where “at least one combination of adjacent two or more (of .. . ) are mutually bonded to form a substituted or unsubstitutedmonocyclic ring, mutually bonded to form a substituted or unsubstitutedfused ring, or not mutually bonded” mentioned herein refer to instanceswhere “at least one combination of adjacent two or more (of . . . ) aremutually bonded to form a substituted or unsubstituted monocyclic ring,“at least one combination of adjacent two or more (of . . . ) aremutually bonded to form a substituted or unsubstituted fused ring,” and“at least one combination of adjacent two or more (of . . . ) are notmutually bonded.”

Instances where “at least one combination of adjacent two or more (of .. . ) are mutually bonded to form a substituted or unsubstitutedmonocyclic ring” and “at least one combination of adjacent two or more(of . . . ) are mutually bonded to form a substituted or unsubstitutedfused ring” mentioned herein (these instances will be sometimescollectively referred to as an instance of “bonded to form a ring”hereinafter) will be described below. An anthracene compound having abasic skeleton in a form of an anthracene ring and represented by aformula (TEMP-103) below will be used as an example for the description.

For instance, when “at least one combination of adjacent two or more ofR₉₂₁ to R₉₃₀ are mutually bonded to form a ring,” the combination ofadjacent ones of R₉₂₁ to R₉₃₀ (i.e. the combination at issue) is acombination of R₉₂₁ and R₉₂₂, a combination of R₉₂₂ and R₉₂₃, acombination of R₉₂₃ and R₉₂₄, a combination of R₉₂₄ and R₉₃₀, acombination of R₉₃₀ and R₉₂₅, a combination of R₉₂₅ and R₉₂₆, acombination of R₉₂₆ and R₉₂₇, a combination of R₉₂₇ and R₉₂₈, acombination of R₉₂₈ and R₉₂₉, or a combination of R₉₂₀ and R₉₂₁.

The term “at least one combination” means that two or more of the abovecombinations of adjacent two or more of R₉₂₁ to R₉₃₀ may simultaneouslyform rings. For instance, when R₉₂₁ and R₉₂₂ are mutually bonded to forma ring QA and R₉₂₅ and R₉₂₆ are simultaneously mutually bonded to form aring Q_(B), the anthracene compound represented by the formula(TEMP-103) is represented by a formula (TEMP-104) below.

The instance where the “combination of adjacent two or more” form a ringmeans not only an instance where the “two” adjacent components arebonded but also an instance where adjacent “three or more” are bonded.For instance, R₉₂₁ and R₉₂₂ are mutually bonded to form a ring QA andR₉₂₂ and R₉₂₃ are mutually bonded to form a ring Qc, and mutuallyadjacent three components (R₉₂₁, R₉₂₂ and R₉₂₃) are mutually bonded toform a ring fused to the anthracene basic skeleton. In this case, theanthracene compound represented by the formula (TEMP-103) is representedby a formula (TEMP-105) below. In the formula (TEMP-105) below, the ringQA and the ring Qc share R₉₂₂.

The formed “monocyclic ring” or “fused ring” may be, in terms of theformed ring in itself, a saturated ring or an unsaturated ring. When the“combination of adjacent two” form a “monocyclic ring” or a “fusedring,” the “monocyclic ring” or “fused ring” may be a saturated ring oran unsaturated ring. For instance, the ring Q_(A) and the ring Q_(B)formed in the formula (TEMP-104) are each independently a “monocyclicring” or a “fused ring.” Further, the ring Q_(A) and the ring Qc formedin the formula (TEMP-105) are each a “fused ring.” The ring Q_(A) andthe ring Qc in the formula (TEMP-105) are fused to form a fused ring.When the ring Q_(A) in the formula (TMEP-104) is a benzene ring, thering Q_(A) is a monocyclic ring. When the ring Q_(A) in the formula(TMEP-104) is a naphthalene ring, the ring Q_(A) is a fused ring.

The “unsaturated ring” represents an aromatic hydrocarbon ring or anaromatic heterocycle. The “saturated ring” represents an aliphatichydrocarbon ring or a non-aromatic heterocycle.

Specific examples of the aromatic hydrocarbon ring include a ring formedby terminating a bond of a group in the specific example of the specificexample group G1 with a hydrogen atom.

Specific examples of the aromatic heterocycle include a ring formed byterminating a bond of an aromatic heterocyclic group in the specificexample of the specific example group G2 with a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include a ringformed by terminating a bond of a group in the specific example of thespecific example group G6 with a hydrogen atom.

The phrase “to form a ring” herein means that a ring is formed only by aplurality of atoms of a basic skeleton, or by a combination of aplurality of atoms of the basic skeleton and one or more optional atoms.For instance, the ring Q_(A) formed by mutually bonding R₉₂₁ and R₉₂₂shown in the formula (TEMP-104) is a ring formed by a carbon atom of theanthracene skeleton bonded to R₉₂₁, a carbon atom of the anthraceneskeleton bonded to R₉₂₂, and one or more optional atoms. Specifically,when the ring Q_(A) is a monocyclic unsaturated ring formed by R₉₂₁ andR₉₂₂, the ring formed by a carbon atom of the anthracene skeleton bondedto R₉₂₁, a carbon atom of the anthracene skeleton bonded to R₉₂₂, andfour carbon atoms is a benzene ring.

The “optional atom” is, unless otherwise specified herein, preferably atleast one atom selected from the group consisting of a carbon atom,nitrogen atom, oxygen atom, and sulfur atom. A bond of the optional atom(e.g. a carbon atom and a nitrogen atom) not forming a ring may beterminated by a hydrogen atom or the like or may be substituted by an“optional substituent” described later. When the ring includes anoptional element other than carbon atom, the resultant ring is aheterocycle.

The number of “one or more optional atoms” forming the monocyclic ringor fused ring is, unless otherwise specified herein, preferably in arange from 2 to 15, more preferably in a range from 3 to 12, furtherpreferably in a range from 3 to 5.

Unless otherwise specified herein, the ring, which may be a “monocyclicring” or “fused ring,” is preferably a “monocyclic ring.”

Unless otherwise specified herein, the ring, which may be a “saturatedring” or “unsaturated ring,” is preferably an “unsaturated ring.”

Unless otherwise specified herein, the “monocyclic ring” is preferably abenzene ring.

Unless otherwise specified herein, the “unsaturated ring” is preferablya benzene ring.

When “at least one combination of adjacent two or more” (of . . . ) are“mutually bonded to form a substituted or unsubstituted monocyclic ring”or “mutually bonded to form a substituted or unsubstituted fused ring,”unless otherwise specified herein, at least one combination of adjacenttwo or more of components are preferably mutually bonded to form asubstituted or unsubstituted “unsaturated ring” formed of a plurality ofatoms of the basic skeleton, and 1 to 15 atoms of at least one elementselected from the group consisting of carbon, nitrogen, oxygen andsulfur.

When the “monocyclic ring” or the “fused ring” has a substituent, thesubstituent is the substituent described in later-described “optionalsubstituent.” When the “monocyclic ring” or the “fused ring” has asubstituent, specific examples of the substituent are the substituentsdescribed in the above under the subtitle “Substituent MentionedHerein.”

When the “saturated ring” or the “unsaturated ring” has a substituent,the substituent is the substituent described in later-described“optional substituent.” When the “monocyclic ring” or the “fused ring”has a substituent, specific examples of the substituent are thesubstituents described in the above under the subtitle “SubstituentMentioned Herein.”

The above is the description for the instances where “at least onecombination of adjacent two or more (of . . . ) are mutually bonded toform a substituted or unsubstituted monocyclic ring” and “at least onecombination of adjacent two or more (of . . . ) are mutually bonded toform a substituted or unsubstituted fused ring” mentioned herein(sometimes referred to as an instance of “bonded to form a ring”).

Substituent for Substituted or Unsubstituted Group

In an exemplary embodiment herein, the substituent for the substitutedor unsubstituted group (sometimes referred to as an “optionalsubstituent” hereinafter) is, for instance, a group selected from thegroup consisting of an unsubstituted alkyl group having 1 to 50 carbonatoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, anunsubstituted alkynyl group having 2 to 50 carbon atoms, anunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,—Si(R₉₀₁)(R₉₀₂)(R₉₀₃), —O—(R₉₀₄), —S—(R₉₀₅), —N(R₉₀₆)(R₉₀₇), a halogenatom, a cyano group, a nitro group, an unsubstituted aryl group having 6to 50 ring carbon atoms, and an unsubstituted heterocyclic group having5 to 50 ring atoms,

R₉₀₁ to R₉₀₇ are each independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to50 ring atoms,

when two or more R₉₀₁ are present, the two or more R₉₀₁ are mutually thesame or different,

when two or more R₉₀₂ are present, the two or more R₉₀₂ are mutually thesame or different,

when two or more R₉₀₃ are present, the two or more R₉₀₃ are mutually thesame or different,

when two or more R₉₀₄ are present, the two or more R₉₀₄ are mutually thesame or different,

when two or more R₉₀₅ are present, the two or more R₉₀₅ are mutually thesame or different,

when two or more R₉₀₆ are present, the two or more R₉₀₆ are mutually thesame or different, and

when two or more R₉₀₇ are present, the two or more R₉₀₇ are mutually thesame or different.

In an exemplary embodiment, the substituent for the substituted orunsubstituted group is selected from the group consisting of an alkylgroup having 1 to 50 carbon atoms, an aryl group having 6 to 50 ringcarbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

In an exemplary embodiment, the substituent for the substituted orunsubstituted group is selected from the group consisting of an alkylgroup having 1 to 18 carbon atoms, an aryl group having 6 to 18 ringcarbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

Specific examples of the above optional substituent are the same as thespecific examples of the substituent described in the above under thesubtitle “Substituent Mentioned Herein.”

Unless otherwise specified herein, adjacent ones of the optionalsubstituents may form a “saturated ring” or an “unsaturated ring,”preferably a substituted or unsubstituted saturated five-membered ring,a substituted or unsubstituted saturated six-membered ring, asubstituted or unsubstituted unsaturated five-membered ring, or asubstituted or unsubstituted unsaturated six-membered ring, morepreferably a benzene ring.

Unless otherwise specified herein, the optional substituent may furtherinclude a substituent. Examples of the substituent for the optionalsubstituent are the same as the examples of the optional substituent.

Herein, numerical ranges represented by “AA to BB” represent a rangewhose lower limit is the value (AA) recited before “to” and whose upperlimit is the value (BB) recited after “to.”

First Exemplary Embodiment Compound

A compound according to a first exemplary embodiment is a compoundrepresented by a formula (1) below.

In the formula (1),

X¹ to X⁵ each independently represent a nitrogen atom or CR¹⁰,

two or more of X¹ to X⁵ are nitrogen atoms,

at least one combination of adjacent two or more of a plurality of R¹⁰are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

Y¹ to Y⁵ each independently represent a nitrogen atom or CR²⁰,

one or more of Y¹ to Y⁵ are nitrogen atoms,

at least one combination of adjacent two or more of a plurality of R²⁰are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

at least one combination of adjacent two or more of a plurality of R⁵are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

at least one combination of adjacent two or more of a plurality of R⁶are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other,

at least one combination of adjacent two or more of a plurality of R⁷are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other;

R¹⁰, R²⁰. and R⁵ to R⁷ forming neither the substituted or unsubstitutedmonocyclic ring nor the substituted or unsubstituted fused ring, and R⁸and R⁹ each independently represent a hydrogen atom, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted alkenylgroup having 2 to 50 carbon atoms, a substituted or unsubstitutedalkynyl group having 2 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a grouprepresented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a group represented by —O—(R₉₀₄),a group represented by —S—(R₉₀₅), a group represented by —N(R₉₀₆)(R₉₀₇),a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to50 ring atoms,

when a plurality of R¹⁰ are present, the plurality of R¹⁰ are mutuallythe same or different,

when a plurality of R²⁰ are present, the plurality of R²⁰ are mutuallythe same or different,

the plurality of R⁵ are mutually the same or different,

the plurality of R⁶ are mutually the same or different,

the plurality of R⁷ are mutually the same or different,

a represents 0, 1, 2, or 3,

when a is 2 or 3, a plurality of L1 are mutually the same or different,

b represents 0, 1, 2, or 3,

when b is 2 or 3, a plurality of L2 are mutually the same or different,

when a and b are each independently 1, 2, or 3, L1 and L2 eachindependently represent a single bond, a substituted or unsubstitutedarylene group having 6 to 50 ring carbon atoms, or a substituted orunsubstituted divalent heterocyclic group having 5 to 50 ring atoms, and

when only one of Y¹ to Y⁵ is a nitrogen atom, L2 is not a single bond,or any of Y¹ to Y⁵ other than a nitrogen atom is not CH.

In the compound represented by the formula (1), R₉₀₁ to R₉₀₇ eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms, or asubstituted or unsubstituted heterocyclic group having 5 to 50 ringatoms, and

when two or more R₉₀₁ are present, the two or more R₉₀₁ are mutually thesame or different; when two or more R₉₀₂ are present, the two or moreR₉₀₂ are mutually the same or different; when two or more R₉₀₃ arepresent, the two or more R₉₀₃ are mutually the same or different; whentwo or more R₉₀₄ are present, the two or more R₉₀₄ are mutually the sameor different; when two or more R₉₀₅ are present, the two or more R₉₀₅are mutually the same or different; when two or more R₉₀₆ are present,the two or more R₉₀₆ are mutually the same or different; and when two ormore R₉₀₇ are present, the two or more R₉₀₇ are mutually the same ordifferent.

A compound in which one substituent including azine is introduced to atriptycene skeleton is known in the related art (e.g., see Documents 1and 2).

The inventors found that introducing at least one substituent includingan azine ring to both terminals of a triptycene skeleton as in thecompound represented by the formula (1) results in a compound capable ofenhancing the performance of an organic EL device, specifically, acompound capable of reducing the drive voltage of an organic EL device.

The compound according to the exemplary embodiment is suitably used as amaterial for electron transporting zone of organic EL device(preferably, as a material for electron transporting layer). When thecompound according to the exemplary embodiment is used as a material forelectron transporting zone, the injectability of electrons to adjacentlayers can be improved and, consequently, the reduction in the voltageof an organic EL device may be further readily achieved.

In the compound according to the exemplary embodiment, it is preferablethat at least one combination of adjacent two or more of a plurality ofR¹⁰ be not bonded to each other, at least one combination of adjacenttwo or more of a plurality of R²⁰ be not bonded to each other, at leastone combination of adjacent two or more of a plurality of R⁵ be notbonded to each other, at least one combination of adjacent two or moreof a plurality of R⁶ be not bonded to each other, and at least onecombination of adjacent two or more of a plurality of R⁷ be not bondedto each other.

In the compound according to the exemplary embodiment, it is preferablethat a combination of adjacent two or more of the plurality of R¹⁰ formneither a substituted or unsubstituted monocyclic ring nor a substitutedor unsubstituted fused ring.

In the compound according to the exemplary embodiment, it is preferablethat a combination of adjacent two or more of the plurality of R²⁰ formneither a substituted or unsubstituted monocyclic ring nor a substitutedor unsubstituted fused ring.

In the compound according to the exemplary embodiment, it is preferablethat a combination of adjacent two or more of the plurality of R⁵ formneither a substituted or unsubstituted monocyclic ring nor a substitutedor unsubstituted fused ring.

In the compound according to the exemplary embodiment, it is preferablethat a combination of adjacent two or more of the plurality of R⁶ formneither a substituted or unsubstituted monocyclic ring nor a substitutedor unsubstituted fused ring.

In the compound according to the exemplary embodiment, it is preferablethat a combination of adjacent two or more of the plurality of R⁷ formneither a substituted or unsubstituted monocyclic ring nor a substitutedor unsubstituted fused ring.

In the formula (1), among partial structures represented by formulae(1A), (1B), and (1C) below, the partial structures represented by theformulae (1A) and (1B) are preferably the same as each other.

In the formula (1), among the partial structures represented by theformulae (1A), (1B), and (1C), the partial structures represented by theformulae (1A) and (1B) are also preferably different from each other.

In the formula (1C), R⁵ to R⁹ each independently represent the same asR⁵ to R⁹ in the formula (1),

in the formula (1A), X¹ to X⁵, L1, and a each independently representthe same as X¹ to X⁵, L1, and a in the formula (1), and * represents abonding position to *1 in the partial structure represented by theformula (1C) in the formula (1), and

in the formula (1B), Y¹ to Y⁵, L2, and b each independently representthe same as Y¹ to Y⁵, L2, and b in the formula (1), and * represents abonding position to *2 in the partial structure represented by theformula (1C) in the formula (1).

In the formula (1A), two or three of X¹ to X⁵ are preferably nitrogenatoms, and

in the formula (1B), one, two, or three of Y¹ to Y⁵ are preferablynitrogen atoms.

In the compound according to the exemplary embodiment, it is preferablethat the partial structure represented by the formula (1A) berepresented by any of formulae (1A-1) to (1A-3) below and the partialstructure represented by the formula (1B) be represented by any offormulae (1B-1) to (1B-6) below.

In the compound according to the exemplary embodiment, it is morepreferable that the partial structure represented by the formula (1A) berepresented by a formula (1A-1) or (1A-2) below and the partialstructure represented by the formula (1B) be represented by a formula(1B-1), (1B-2), or (1B-3) below.

In the formulae (1A-1) to (1A-3), L1 and a each independently representthe same as L1 and a in the formula (1); and R¹¹, R¹², R¹³, and R¹⁴ eachindependently represent the same as R¹⁰ in the formula (1).

In the formulae (1B-1) to (1B-6), L2 and b each independently representthe same as L2 and b in the formula (1); and R²¹ to R²⁵ eachindependently represent the same as R²⁰ in the formula (1).

In the compound according to the exemplary embodiment,

when the partial structure represented by the formula (1A) isrepresented by the formula (1A-1), the partial structure represented bythe formula (1B) is preferably represented by the formula (1B-1),

when the partial structure represented by the formula (1A) isrepresented by the formula (1A-2), the partial structure represented bythe formula (1B) is preferably represented by the formula (1B-2); and

when the partial structure represented by the formula (1A) isrepresented by the formula (1A-3), the partial structure represented bythe formula (1B) is preferably represented by the formula (1B-4).

Embodiments of the compound according to the exemplary embodiment inwhich the partial structure represented by the formula (1A) isrepresented by the formula (1A-1) and the partial structure representedby the formula (1B) is represented by the formula (1B-1) include anembodiment where the partial structures and the substituents thereof arecompletely the same and an embodiment where the partial structures arenot completely the same.

The embodiment where the partial structures and the substituents thereofare completely the same is an embodiment where, in the formulae (1A-1)and (1B-1), R¹² and R²² are mutually the same, R¹⁴ and R²⁴ are mutuallythe same, L1 and L2 are mutually the same, and a and b are mutually thesame. The embodiment where the partial structures are not completely thesame is an embodiment where, in the formulae (1A-1) and (1B-1), at leastone of the pairs of R¹² and R²², R¹⁴ and R²⁴, L1 and L2, and a and b aremutually different. In the formulae (1A-1) and (1B-1), “R¹² and R²²” maytranslate to “R¹² and R²⁴”, and “R¹⁴ and R²⁴” may translate to “R¹⁴ andR²²”.

Similarly, in an embodiment where the partial structure represented bythe formula (1A) is represented by the formula (1A-2) and the partialstructure represented by the formula (1B) is represented by the formula(1B-2) and in an embodiment where the partial structure represented bythe formula (1A) is represented by the formula (1A-3) and the partialstructure represented by the formula (1B) is represented by the formula(1B-4), the partial structures and the substituents thereof may becompletely the same and may not be completely the same. In the formulae(1A-3) and (1B-4), “R¹² and R²²” may translate to “R¹² and R²⁴” and “R¹⁴and R²⁴” may translate to “R¹⁴ and R²²”.

In the compound according to the exemplary embodiment, the partialstructure represented by the formula (1A) and the partial structurerepresented by the formula (1B) and the substituents thereof may becompletely the same and may not be completely the same.

In the compound according to the exemplary embodiment, the compoundrepresented by the formula (1) is preferably a compound represented by aformula (10) below.

In the formula (10), X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and beach independently represent the same as X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ toR⁹, L1, L2, a, and b in the formula (1), and

R¹² and R¹⁴ each independently represent the same as R¹⁰ in the formula(1); and R²² and R²⁴ each independently represent the same as R²⁰ in theformula (1).

In the compound according to the exemplary embodiment, the compoundrepresented by the formula (1) is preferably a compound represented by aformula (10-1a) below or an enantiomer of the compound represented bythe formula (10-1a).

Enantiomers are a pair of stereoisomers that are non-superimposablemirror images.

The enantiomer of the compound represented by the formula (10-1a) can berepresented by a formula (10-1b) below.

Herein, the structure of one of a pair of enantiomers may be describedas a representative.

When the compound according to the exemplary embodiment is used, onlyone of the enantiomers may be used alone and the other enantiomer may bealso used alone. Or, as described in a second exemplary embodimentbelow, a mixture including one of the enantiomers (first compound) andthe other enantiomer (second compound) may be used.

In the formulae (10-1a) and (10-1b),

X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and b each independentlyrepresent the same as X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and bin the formula (1), and

R¹² and R¹⁴ each independently represent the same as R¹⁰ in the formula(1); and R²² and R²⁴ each independently represent the same as R²⁰ in theformula (1).

In the compound according to the exemplary embodiment, the compoundrepresented by the formula (1) is also preferably a compound representedby a formula (10-2a) below or an enantiomer of the compound representedby the formula (10-2a).

The enantiomer of the compound represented by the formula (10-2a) can berepresented by, for example, a formula (10-2b) below.

In the formulae (10-2a) and (10-2b),

X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and b each independentlyrepresent the same as X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and bin the formula (1), and

R¹² and R¹⁴ each independently represent the same as R¹⁰ in the formula(1); and R²² and R²⁴ each independently represent the same as R²⁰ in theformula (1).

In the compound according to the exemplary embodiment, the compoundrepresented by the formula (1) is also preferably a compound representedby a formula (10-3a) below or an enantiomer of the compound representedby the formula (10-3a).

The enantiomer of the compound represented by the formula (10-3a) can berepresented by, for example, a formula (10-3b) below.

In the formulae (10-3a) and (10-3b),

X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and b each independentlyrepresent the same as X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and bin the formula (1), and

R¹² and R¹⁴ each independently represent the same as R¹⁰ in the formula(1); and R²² and R²⁴ each independently represent the same as R²⁰ in theformula (1).

In the compound according to the exemplary embodiment, it is preferablethat L1 and L2 each independently represent a single bond, a substitutedor unsubstituted arylene group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted divalent heterocyclic group having 5 to 30ring atoms.

In the compound according to the exemplary embodiment, it is preferablethat L1 and L2 each independently represent a single bond, a substitutedor unsubstituted phenylene group, a substituted or unsubstitutedbiphenylene group, a substituted or unsubstituted terphenylene group, asubstituted or unsubstituted naphthylene group, a substituted orunsubstituted phenanthrylene group, a substituted or unsubstitutedfluorenylene group, a substituted or unsubstituted dibenzofuranylenegroup, a substituted or unsubstituted dibenzothienylene group, asubstituted or unsubstituted pyridylene group, or a substituted orunsubstituted quinolylene group.

In the compound according to the exemplary embodiment, a is preferably 0or 1.

In the compound according to the exemplary embodiment, b is preferably 0or 1.

In the compound according to the exemplary embodiment, it is alsopreferable that L1 and L2 each independently represent at least onegroup selected from the group consisting of groups represented byformulae (L-1) to (L-16) below.

In the formulae (L-1) to (L-16), Q₁ to Q₁₄ preferably each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 18 ring carbon atoms, a substituted or unsubstitutedaryl group having 6 to 18 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 18 ring atoms, and morepreferably each independently represent a hydrogen atom, anunsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstitutedcycloalkyl group having 3 to 18 ring carbon atoms, an unsubstituted arylgroup having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclicgroup having 5 to 18 ring atoms.

In the compound according to the exemplary embodiment, R¹⁰, R²⁰, and R⁵to R⁹ preferably each independently represent a hydrogen atom, a halogenatom, a cyano group, a substituted or unsubstituted alkyl group having 1to 50 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 50 ring carbon atoms, a group represented by—Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a group represented by —O—(R₉₀₄), a grouprepresented by —N(R₉₀₆)(R₉₀₇), a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, or a substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms.

In the compound according to the exemplary embodiment, R¹⁰, R²⁰, and R⁵to R⁹ preferably each independently represent a hydrogen atom, a halogenatom, a cyano group, a substituted or unsubstituted alkyl group having 1to 18 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 18 ring carbon atoms, a substituted or unsubstituted arylgroup having 6 to 18 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 18 ring atoms.

In the compound according to the exemplary embodiment, R¹⁰, R²⁰, and R⁵to R⁹ preferably each independently represent a hydrogen atom or a grouprepresented by any of formulae (A1) to (A31) below.

In the formulae (A1) to (A31),

Z₁ represents an oxygen atom, a sulfur atom, or NRb₃;

at least one combination of adjacent two or more of a plurality of Raare bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other;

a pair of Rb₁ and Rb₂ are bonded to each other to form a substituted orunsubstituted monocyclic ring, are bonded to each other to form asubstituted or unsubstituted fused ring, or are not bonded to eachother;

Rb₁ and Rb₂ forming neither the substituted or unsubstituted monocyclicring nor the substituted or unsubstituted fused ring and Rb₃ eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 30 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 30 ring carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heterocyclic group having 5 to 30 ringatoms,

Ra forming neither the substituted or unsubstituted monocyclic ring northe substituted or unsubstituted fused ring each independently representa hydrogen atom, a halogen atom, a cyano group, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a grouprepresented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a group represented by —O—(R₉₀₄),a group represented by —N(R₉₀₆)(R₉₀₇), a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 30 ring atoms,

R₉₀₁ to R₉₀₄, R₉₀₆, and R₉₀₇ each independently represent the same asR₉₀₁ to R₉₀₄, R₉₀₆, and R₉₀₇ in the formula (1),

a plurality of Ra are mutually the same or different,

when a plurality of Z₁ are present, the plurality of Z₁ are mutually thesame or different,

when a plurality of Rb₁ are present, the plurality of Rb₁ are mutuallythe same or different,

when a plurality of Rb₂ are present, the plurality of Rb₂ are mutuallythe same or different, and

when a plurality of Rb₃ are present, the plurality of Rb₃ are mutuallythe same or different.

It is also preferable that, in the formulae (A1) to (A31), a combinationof adjacent two or more of the plurality of Ra form neither asubstituted or unsubstituted monocyclic ring nor a substituted orunsubstituted fused ring.

It is also preferable that, in the formula (A14), Rb₁ and Rb₂ be bondedto each other to form a substituted or unsubstituted monocyclic ring orbe bonded to each other to form a substituted or unsubstituted fusedring.

In the formulae (A1) to (A31), Rb₁, Rb₂, Rb₃, and Ra preferably eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 18 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 18 ring carbon atoms, a substituted orunsubstituted aryl group having 6 to 18 ring carbon atoms, or asubstituted or unsubstituted heterocyclic group having 5 to 18 ringatoms, and more preferably each independently represent a hydrogen atom,an unsubstituted alkyl group having 1 to 18 carbon atoms, anunsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, anunsubstituted aryl group having 6 to 18 ring carbon atoms, or anunsubstituted heterocyclic group having 5 to 18 ring atoms.

In the compound according to the exemplary embodiment, R⁵ to R⁹preferably represent a hydrogen atom, and R¹⁰ and R²⁰ preferably eachindependently represent a hydrogen atom, a halogen atom, a cyano group,a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 18 ringcarbon atoms, a substituted or unsubstituted aryl group having 6 to 18ring carbon atoms, or a substituted or unsubstituted heterocyclic grouphaving 5 to 18 ring atoms.

In the compound according to the exemplary embodiment, R₉₀₁ to R₉₀₇preferably each independently represent a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 18 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, asubstituted or unsubstituted aryl group having 6 to 18 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to18 ring atoms, and more preferably each independently represent ahydrogen atom, an unsubstituted alkyl group having 1 to 18 carbon atoms,an unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, anunsubstituted aryl group having 6 to 18 ring carbon atoms, or anunsubstituted heterocyclic group having 5 to 18 ring atoms.

Manufacturing Method of Compound According to Exemplary Embodiment

The compound according to the exemplary embodiment can be manufacturedaccording to, for instance, a method described later in Examples. Thecompound of the exemplary embodiment can be manufactured, for instance,by application of known substitution reactions and/or materials tailoredfor a target compound according to reactions described later inExamples.

Specific examples of the compound according to the exemplary embodimentinclude the following compounds. Note that the invention is not limitedto the specific examples of the compound.

When the compound according to the exemplary embodiment is anenantiomer, only one of the structures is illustrated as arepresentative.

Second Exemplary Embodiment Mixture

A mixture according to the second exemplary embodiment includes thecompound according to the first exemplary embodiment as a first compoundand a second compound that is an enantiomer of the first compound.

Examples of the combination of the compounds included in the mixtureaccording to the second exemplary embodiment include:

a combination of the compound represented by the formula (10-1a) thatserves as a first compound and the compound represented by the formula(10-1b) that serves as a second compound;

a combination of the compound represented by the formula (10-2a) thatserves as a first compound and the compound represented by the formula(10-2b) that serves as a second compound; and

a combination of the compound represented by the formula (10-3a) thatserves as a first compound and the compound represented by the formula(10-3b) that serves as a second compound.

The mixture according to the second exemplary embodiment can be suitablyused as a material for an electron transporting zone (preferably, amaterial for an electron transporting layer) of an organic EL device.

The mixture according to the second exemplary embodiment may furtherinclude another compound in addition to the first compound (the compoundaccording to the first exemplary embodiment) and the second compoundthat is an enantiomer of the first compound.

According to the second exemplary embodiment, a mixture capable ofenhancing the performance of an organic EL device and, in particular, amixture capable of reducing the drive voltage of an organic EL devicecan be provided.

Specific examples [1] to [10] of the combination of the first and secondcompounds included in the mixture according to the second exemplaryembodiment are described below. Note that the mixture according to theinvention is not limited to the specific examples below.

Third Exemplary Embodiment Material for Organic ElectroluminescenceDevice

A material for organic EL device according to a third exemplaryembodiment includes the compound according to the first exemplaryembodiment. For example, the material for organic EL device may includeonly the compound according to the first exemplary embodiment. Inanother case, the material for organic EL device may include thecompound according to the first exemplary embodiment and a compoundother than the compound according to the first exemplary embodiment. Theother compound may be, but is not necessarily, an enantiomer of thecompound according to the first exemplary embodiment.

The material for organic EL device according to the third exemplaryembodiment can be suitably used as a material for an electrontransporting zone (preferably, a material for an electron transportinglayer) of an organic EL device.

According to the third exemplary embodiment, a material for organic ELdevice capable of enhancing the performance of an organic EL device and,in particular, a material for organic EL device capable of reducing thedrive voltage of an organic EL device can be provided.

Fourth Exemplary Embodiment Material for Organic ElectroluminescenceDevice

A material for organic EL device according to a fourth exemplaryembodiment includes the mixture according to the second exemplaryembodiment. For example, the material for organic EL device may includeonly the mixture according to the second exemplary embodiment. Inanother case, the material for organic EL device may include the mixtureaccording to the second exemplary embodiment and another compound.Examples of the another compound include any other compound than thefirst and second compounds included in the mixture according to thesecond exemplary embodiment.

The material for organic EL device according to the fourth exemplaryembodiment can be suitably used as a material for an electrontransporting zone (preferably, a material for an electron transportinglayer) of an organic EL device.

According to the fourth exemplary embodiment, a material for organic ELdevice capable of enhancing the performance of an organic EL device and,in particular, a material for organic EL device capable of reducing thedrive voltage of an organic EL device can be provided.

Fifth Exemplary Embodiment Organic Electroluminescence Device

An organic EL device according to a fifth exemplary embodiment includesa cathode, an anode, and an organic layer interposed between the cathodeand the anode. The organic layer includes at least one layer formed froman organic compound. In another case, the organic layer is formed by aplurality of layers that are formed from an organic compound and stackedon top of each other. The organic layer may further include an inorganiccompound.

It is preferable that the organic EL device according to the fifthexemplary embodiment include one or more organic layers and at least oneof the organic layers include the compound according to the firstexemplary embodiment as a first compound.

It is also preferable that the organic EL device according to the fifthexemplary embodiment include one or more organic layers and at least oneof the organic layers include a second compound that is an enantiomer ofthe first compound.

It is also preferable that the organic EL device according to the fifthexemplary embodiment include one or more organic layers and at least oneof the organic layers include the first compound and the second compoundthat is an enantiomer of the first compound, that is, the mixtureaccording to the second exemplary embodiment.

The organic layer may be formed by, for example, one emitting layer ormay include layer(s) that may be included in an organic EL device.Examples of the layers that may be included in an organic EL deviceinclude, but are not limited to, at least one layer selected from thegroup consisting of a hole injecting layer, a hole transporting layer,an electron injecting layer, an electron transporting layer, an electronblocking layer, and a hole blocking layer.

The compound according to the first exemplary embodiment (firstcompound), the second compound that is an enantiomer of the firstcompound, and the mixture according to the second exemplary embodimentcan be suitably used as a material for an electron transporting zone,preferably used as a material for an electron transporting layer or ahole blocking layer, and more preferably used as a material for anelectron transporting layer, of a fluorescent or phosphorescent organicEL device.

In the organic EL device according to the fifth exemplary embodiment, itis preferable that the organic layer include an emitting layerinterposed between the cathode and the anode and an electrontransporting layer interposed between the cathode and the emitting layerand that the electron transporting layer include the first compound orthe second compound that is an enantiomer of the first compound.

In the organic EL device according to the fifth exemplary embodiment, itis also preferable that the organic layer include an emitting layerinterposed between the cathode and the anode and an electrontransporting layer interposed between the cathode and the emitting layerand that the electron transporting layer include the first compound andthe second compound that is an enantiomer of the first compound, thatis, the mixture according to the second exemplary embodiment.

In the organic EL device according to the fifth exemplary embodiment, itis preferable that the electron transporting layer include a firstelectron transporting layer interposed between the cathode and theemitting layer and a second electron transporting layer interposedbetween the first electron transporting layer and the cathode and thatthe second electron transporting layer include the first compound or thesecond compound that is an enantiomer of the first compound.

In the organic EL device according to the fifth exemplary embodiment, itis also preferable that the electron transporting layer include a firstelectron transporting layer interposed between the cathode and theemitting layer and a second electron transporting layer interposedbetween the first electron transporting layer and the cathode and thatthe second electron transporting layer include the first compound andthe second compound that is an enantiomer of the first compound, thatis, the mixture according to the second exemplary embodiment.

The organic EL device according to the fifth exemplary embodiment may bea fluorescent or phosphorescent monochromatic emitting device or afluorescent-phosphorescent hybrid white emitting device. The organic ELdevice according to the fifth exemplary embodiment may be a simpleorganic EL device including a single emitting unit or a tandem organicEL device including a plurality of emitting units. It is particularlypreferable that the organic EL device according to the fifth exemplaryembodiment be a fluorescent device. The term “emitting unit” used hereinrefers to the organic layers. At least one of the organic layers is theemitting layer. The emitting unit is a minimum unit that emits lightupon the recombination of the holes and electrons injected.

A typical device arrangement of the simple organic EL device is, forexample, as follows:

(1) Anode/Emitting Unit (Organic Layers)/Cathode

The emitting unit may be a multilayer emitting unit that includes aplurality of phosphorescent and fluorescent emitting layers. In such acase, a space layer may be interposed between the emitting layers inorder to prevent excitons generated in the phosphorescent emitting layerfrom being diffused into the fluorescent emitting layer. Typical layerarrangements of the simple emitting unit are described below. Note thatthe parenthesized layers are optional.

(a) (Hole injecting layer/) Hole transporting layer/Fluorescent emittinglayer/Electron transporting layer (/Electron injecting layer)

(b) (Hole injecting layer/) Hole transporting layer/Phosphorescentemitting layer/Electron transporting layer (/Electron injecting layer)

(c) (Hole injecting layer/) Hole transporting layer/First fluorescentemitting layer/Second fluorescent emitting layer/Electron transportinglayer (/Electron injecting layer)

(d) (Hole injecting layer/) Hole transporting layer/First phosphorescentemitting layer/Second phosphorescent emitting layer/Electrontransporting layer (/Electron injecting layer)

(e) (Hole injecting layer/) Hole transporting layer/Phosphorescentemitting layer/Space layer/Fluorescent emitting layer/Electrontransporting layer (/Electron injecting layer)

(f) (Hole injecting layer/) Hole transporting layer/First phosphorescentemitting layer/Second phosphorescent emitting layer/Spacelayer/Fluorescent emitting layer/Electron transporting layer (/Electroninjecting layer)

(g) (Hole injecting layer/) Hole transporting layer/First phosphorescentemitting layer/Space layer/Second phosphorescent emitting layer/Spacelayer/Fluorescent emitting layer/Electron transporting layer (/Electroninjecting layer)

(h) (Hole injecting layer/) Hole transporting layer/Phosphorescentemitting layer/Space layer/First fluorescent emitting layer/Secondfluorescent emitting layer/Electron transporting layer (/Electroninjecting layer)

(i) (Hole injecting layer/) Hole transporting layer/Electron blockinglayer/Fluorescent emitting layer/Electron transporting layer (/Electroninjecting layer)

(j) (Hole injecting layer/) Hole transporting layer/Electron blockinglayer/Phosphorescent emitting layer/Electron transporting layer(/Electron injecting layer)

(k) (Hole injecting layer/) Hole transporting layer/Exciton blockinglayer/Fluorescent emitting layer/Electron transporting layer (/Electroninjecting layer)

(l) (Hole injecting layer/) Hole transporting layer/Exciton blockinglayer/Phosphorescent emitting layer/Electron transporting layer(/Electron injecting layer)

(m) (Hole injecting layer/) First hole transporting layer/Second holetransporting layer/Fluorescent emitting layer/Electron transportinglayer (/Electron injecting layer)

(n) (Hole injecting layer/) First hole transporting layer/Second holetransporting layer/Phosphorescent emitting layer/Electron transportinglayer (/Electron injecting layer)

(o) (Hole injecting layer/) First hole transporting layer/Second holetransporting layer/Fluorescent emitting layer/First electrontransporting layer/Second electron transporting layer (/Electroninjecting layer)

(p) (Hole injecting layer/) First hole transporting layer/Second holetransporting layer/Phosphorescent emitting layer/First electrontransporting layer/Second electron transporting layer (/Electroninjecting layer)

(q) (Hole injecting layer/) Hole transporting layer/Fluorescent emittinglayer/Hole blocking layer/Electron transporting layer (/Electroninjecting layer)

(r) (Hole injecting layer/) Hole transporting layer/Phosphorescentemitting layer/Hole blocking layer/Electron transporting layer(/Electron injecting layer)

(s) (Hole injecting layer/) Hole transporting layer/Fluorescent emittinglayer/Exciton blocking layer/Electron transporting layer (/Electroninjecting layer)

(t) (Hole injecting layer/) Hole transporting layer/Phosphorescentemitting layer/Exciton blocking layer/Electron transporting layer(/Electron injecting layer)

The colors of light emitted by the above phosphorescent or fluorescentemitting layers may be mutually different. Specifically, the aboveemitting unit (f) may have, for example, the following layerarrangement: (Hole injecting layer/) Hole transporting layer/Firstphosphorescent emitting layer (emits red light)/Second phosphorescentemitting layer (emits green light)/Space layer/Fluorescent emittinglayer (emits blue light)/Electron transporting layer.

Optionally, an electron blocking layer may be interposed between eachemitting layer and the hole transporting layer or space layer as needed.Further, a hole blocking layer may be interposed between each emittinglayer and the electron transporting layer as needed. The electronblocking layer or hole blocking layer enables electrons or holes to beconfined in the emitting layer, thereby increasing the probability ofcharge recombination in the emitting layer, and consequently enhancingluminous efficiency.

A typical device arrangement of the tandem organic EL device is, forexample, as follows:

(2) Anode/First Emitting Unit/Intermediate Layer/Second EmittingUnit/Cathode

The first and second emitting units can be each independently selectedfrom, for example, the above-described emitting units.

The intermediate layer is commonly also referred to as an intermediateelectrode, intermediate conductive layer, charge generating layer,electron drawing layer, connection layer, or intermediate insulationlayer. The intermediate layer may be formed from a known materialcapable of feeding electrons and holes to the first and second emittingunits, respectively.

FIG. 1 is a schematic diagram of an exemplary arrangement of the organicEL device according to the invention. An organic EL device 1 includes asubstrate 2, an anode 3, a cathode 4, and an emitting unit (organiclayers) 10 interposed between the anode 3 and the cathode 4. Theemitting unit 10 includes an emitting layer 5. A hole transporting zone6 (hole injecting layer, hole transporting layer, and the like) isinterposed between the emitting layer 5 and the anode 3. An electrontransporting zone 7 (electron injecting layer, electron transportinglayer, and the like) is interposed between the emitting layer 5 and thecathode 4. Optionally, an electron blocking layer (not illustrated inthe drawing) may be provided on a side of the emitting layer 5 close tothe anode 3, and a hole blocking layer (not illustrated in the drawing)may be provided on a side of the emitting layer 5 close to the cathode4. This enables electrons and holes to be confined in the emitting layer5 and consequently further increases the efficiency with which excitonsare generated in the emitting layer 5.

FIG. 2 is a schematic diagram of another exemplary arrangement of theorganic EL device according to the invention. An organic EL device 11includes a substrate 2, an anode 3, a cathode 4, and an emitting unit(organic layers) 20 interposed between the anode 3 and the cathode 4.The emitting unit 20 includes an emitting layer 5. A hole transportingzone interposed between the anode 3 and the emitting layer 5 is formedby a hole injecting layer 6 a, a first hole transporting layer 6 b, anda second hole transporting layer 6 c. An electron transporting zoneinterposed between the emitting layer 5 and the cathode 4 is formed by afirst electron transporting layer 7 a and a second electron transportinglayer 7 b.

In the exemplary embodiment, a host combined with a fluorescent dopant(fluorescent material) is referred to as a fluorescent host, and a hostcombined with a phosphorescent dopant is referred to as a phosphorescenthost. Note that the fluorescent and phosphorescence hosts are notdistinguished from each other only by the molecular structure. In otherwords, the phosphorescence host is a material for forming aphosphorescent emitting layer including a phosphorescent dopant, and itdoes not mean that the phosphorescence host cannot be used as a materialfor forming a fluorescent emitting layer. The same applies to thefluorescent host.

The arrangement of the organic EL device is further described below.Hereinafter, reference numerals may be omitted.

Substrate

The substrate is used as a support for the organic EL device. Forinstance, glass, quartz, plastics and the like are usable for thesubstrate. A flexible substrate is also usable. The flexible substrateis a bendable substrate, which is exemplified by a plastic substrate.Examples of the material for the plastic substrate includepolycarbonate, polyarylate, polyethersulfone, polypropylene, polyester,polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylenenaphthalate. Moreover, an inorganic vapor deposition film is alsousable.

Anode

Metal, an alloy, an electrically conductive compound, a mixture thereof,or the like having a large work function (specifically, 4.0 eV or more)is preferably used as the anode formed on the substrate. Specificexamples of the material include ITO (Indium Tin Oxide), indiumoxide-tin oxide containing silicon or silicon oxide, indium oxide-zincoxide, indium oxide containing tungsten oxide and zinc oxide, andgraphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten(W), chrome (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu),palladium (Pd), titanium (Ti), and nitrides of the metal (e.g., titaniumnitride) are usable.

The material is typically formed into a film by a sputtering method. Forinstance, the indium oxide-zinc oxide can be formed into a film by thesputtering method using a target in which zinc oxide in a range from 1mass % to 10 mass % is added to indium oxide. Moreover, for instance,the indium oxide containing tungsten oxide and zinc oxide can be formedby the sputtering method using a target in which tungsten oxide in arange from 0.5 mass % to 5 mass % and zinc oxide in a range from 0.1mass % to 1 mass % are added to indium oxide. In addition, the anode maybe formed by a vacuum deposition method, a coating method, an inkjetmethod, a spin coating method or the like.

Among the organic layers formed on the anode, since the hole injectinglayer adjacent to the anode is formed of a material into which holes areeasily injectable irrespective of the work function of the anode, amaterial usable as an electrode material (e.g., metal, an alloy, anelectroconductive compound, a mixture thereof, and the elementsbelonging to the group 1 or 2 of the periodic table) is also usable forthe anode.

A material having a small work function such as elements belonging toGroups 1 and 2 in the periodic table of the elements, specifically, analkali metal such as lithium (Li) and cesium (Cs), an alkaline earthmetal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys(e.g., MgAg and AlLi) including the alkali metal or the alkaline earthmetal, a rare earth metal such as europium (Eu) and ytterbium (Yb),alloys including the rare earth metal are also usable for the anode. Itshould be noted that the vacuum deposition method and the sputteringmethod are usable for forming the anode using the alkali metal, alkalineearth metal and the alloy thereof. Further, when a silver paste is usedfor the anode, the coating method and the inkjet method are usable.

Hole Injecting Layer

The hole injecting layer is a layer including a material having highhole injectability and is interposed between the anode and the emittinglayer or, when a hole transporting layer is present, between the holetransporting layer and the anode.

Examples of the material having high hole injectability includemolybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide,ruthenium oxide, chrome oxide, zirconium oxide, hafnium oxide, tantalumoxide, silver oxide, tungsten oxide, and manganese oxide.

Examples of the highly hole-injectable material further include: anaromatic amine compound, which is a low-molecule organic compound, suchthat 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation:TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA),4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation:DPAB),4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl(abbreviation: DNTPD),1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene(abbreviation: DPA3B),3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA1),3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA2), and3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole(abbreviation: PCzPCN1); anddipyrazino[2,34:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(HAT-CN).

A high polymer compound (e.g., oligomer, dendrimer and polymer) isusable as the material exhibiting a high hole injectability. Examples ofthe high-molecule compound include poly(N-vinylcarbazole) (abbreviation:PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA),poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N-phenylamino}phenyl)methacrylamide](abbreviation: PTPDMA), andpoly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation:Poly-TPD). Moreover, an acid-added high polymer compound such aspoly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS)and polyaniline/poly(styrene sulfonic acid)(PAni/PSS) are also usable.

It is also preferable to use an acceptor material, such as ahexaazatriphenylene (HAT) compound represented by a formula (K) below.

In the formula (K), R₂₁ to R₂₆ each independently represent a cyanogroup, —CONH₂, a carboxyl group, or —COOR₂₇ (where R₂₇ represents analkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3to 20 carbon atoms); and adjacent two selected from R₂₁ and R₂₂, R₂₃ andR₂₄, and R₂₅ and R₂₆ may be bonded to each other to form a grouprepresented by —CO—O—CO—.

Examples of R₂₇ include a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, at-butyl group, a cyclopentyl group, and a cyclohexyl group.

Hole Transporting Layer

The hole transporting layer is a layer including a material having highhole transportability (hole transporting material) and is interposedbetween the anode and the emitting layer or, when a hole injecting layeris present, between the hole injecting layer and the emitting layer.

The hole transporting layer may have a single-layer structure or amultilayer structure. For example, the hole transporting layer may havea two-layer structure including a first hole transporting layer (anodeside) and a second hole transporting layer (cathode side). In anexemplary arrangement of the exemplary embodiment, the hole transportinglayer having a single-layer structure is preferably arranged adjacent tothe emitting layer, and one of the hole transporting layers included inthe multilayer structure closest to the cathode, that is, for example,the second hole transporting layer included in the above two-layerstructure, is preferably arranged adjacent to the emitting layer. Inanother exemplary arrangement of the exemplary embodiment, for example,the electron blocking layer described below may be interposed betweenthe hole transporting layer having a single-layer structure and theemitting layer or between one of the hole transporting layers includedin the multilayer structure closest to the emitting layer and theemitting layer.

An aromatic amine compound, carbazole derivative, anthracene derivativeand the like are usable for the hole transporting layer.

Examples of the aromatic amine compound include4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine(abbreviation: BAFLP),4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine(abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA), and4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB). The above-described substances mostly have a holemobility of 10⁻⁶ cm²/(V.$) or more.

Examples of the carbazole derivative include4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP),9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation:PCzPA).

Examples of the anthracene derivative include2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and9,10-diphenylanthracene (abbreviation: DPAnth).

A high polymer compound such as poly(N-vinylcarbazole) (abbreviation:PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) is alsousable.

Note that a compound other than the above-described one may be also usedwhen the other compound has hole transportability higher than electrontransportability.

Dopant Material for Emitting Layer

The emitting layer is a layer including a highly emittable material(dopant material). Various materials can be used. For example, afluorescent material and a phosphorescent material can be used as adopant material. The fluorescent material is a compound that emits lightin a singlet state. The phosphorescent material is a compound that emitslight in a triplet state.

Examples of a blue fluorescent material usable for the emitting layerinclude a pyrene derivative, styrylamine derivative, chrysenederivative, fluoranthene derivative, fluorene derivative, diaminederivative, and triarylamine derivative. Specific examples includeN,N′-bis[4-(9H-carbazole-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine(abbreviation: YGA2S),4-(9H-carbazole-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine(abbreviation: YGAPA), and4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazole-3-yl)triphenylamine(abbreviation: PCBAPA).

Examples of a green fluorescent material usable for the emitting layerinclude an aromatic amine derivative. Specific examples of the greenfluorescent material includeN-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCABPhA),N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N-triphenyl-1,4-phenylenediamine(abbreviation: 2DPABPhA),N-[9,10-bis(1,1′-biphenyl-2-yl)]—N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine(abbreviation: 2YGABPhA), N,N,9-triphenylanthracene-9-amine(abbreviation: DPhAPhA).

Examples of a red fluorescent material usable for the emitting layerinclude a tetracene derivative and a diamine derivative. Specificexamples includeN,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation:p-mPhTD), and7,14-diphenyl-N,N,N′,N-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine(abbreviation: p-m PhAFD).

Examples of a blue phosphorescent material usable for the emitting layerinclude metal complexes such as an iridium complex, osmium complex andplatinum complex. Specific examples includebis[2-(4′,6′-difluorophenyl)pyridinato-N,C2liridium(III)tetrakis(1-pyrazolyl)borate(abbreviation: FIr6),bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)picolinate(abbreviation: Flrpic),bis[2-(3′,5′bistrifluoromethylphenyl)pyridinato-N,C2liridium(III)picolinate(abbreviation: Ir(CF3ppy)2(pic)), andbis[2-(4′,6′-difluorophenyl)pyridinato-N,C2liridium(III)acetylacetonato(abbreviation: Flracac).

Examples of a green phosphorescent material usable for the emittinglayer include an iridium complex. Specific examples includetris(2-phenylpyridinato-N,C2′)iridium(III) (abbreviation: Ir(ppy)₃),bis(2-phenylpyridinato-N,C2′)iridium(III)acetylacetonato (abbreviation:Ir(ppy)₂(acac)),bis(1,2-diphenyl-1H-benzimidazolato)iridium(III)acetylacetonato(abbreviation: Ir(pbi)₂(acac)), andbis(benzo[h]quinolinato)iridium(III)acetylacetonato (abbreviation:Ir(bzq)₂(acac)). Examples of a red phosphorescent material usable forthe emitting layer include metal complexes such as an iridium complex,platinum complex, terbium complex, and europium complex. Specificexamples include organic metal complexes such asbis[2-(2′-benzo[4,5-α]thienyl)pyridinato-N,C3liridium(III)acetylacetonato(abbreviation: Ir(btp)₂(acac)),bis(1-phenylisoquinolinato-N,C2′)iridium(III)acetylacetonato(abbreviation: Ir(piq)₂(acac)),(acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinolinato]iridium(III)(abbreviation: Ir(Fdpq)₂(acac)), and2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II)(abbreviation: PtOEP).

Moreover, since a rare-earth metal complex, examples of which includetris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation:Tb(acac)₃(Phen)),tris(1,3-diphenyl-1,3-propanedionatodionato)(monophenanthroline)europium(III)(abbreviation: Eu(DBM)₃(Phen)), andtris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III)(abbreviation: Eu(TTA)₃(Phen)), emits light from rare-earth metal ions(electron transition between different multiplicities), the rare-earthmetal complex is usable as a phosphorescent material.

Host Material For Emitting Layer

The emitting layer may have a structure formed by dispersing theabove-described dopant material in another material (host material). Itis preferable to use a material having higher Lowest UnoccupiedMolecular Orbital (LUMO level) and lower Highest Occupied MolecularOrbital (HOMO level) than the dopant material.

Examples of the host material include:

(1) a metal complex such as an aluminum complex, beryllium complex, orzinc complex;

(2) a heterocyclic compound such as an oxadiazole derivative,benzimidazole derivative, or phenanthroline derivative;

(3) a fused aromatic compound such as a carbazole derivative, anthracenederivative, phenanthrene derivative, pyrene derivative, or chrysenederivative; and

(4) an aromatic amine compound such as a triarylamine derivative or afused polycylic aromatic amine derivative.

Specific examples include: metal complexes such astris(8-quinolinolato)aluminum(III) (abbreviation: Alq),tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq₃),bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);

a heterocyclic compound such as2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene(abbreviation: OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole(abbreviation: TAZ),2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)(abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen),bathocuproine (abbreviation: BCP);

a fused aromatic compound such as9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA),3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole(abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene(abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA),2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,9′-bianthryl (abbreviation: BANT),9,9′-(stilbene-3,3′-diyl)diphenanthrene (abbreviation: DPNS),9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2), 3,3′,3″-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3),9,10-diphenylanthracene (abbreviation: DPAnth),6,12-dimethoxy-5,11-diphenylchrysene; and

an aromatic amine compound, such asN,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine(abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine(abbreviation: DPhPA),N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine(abbreviation: PCAPA),N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine(abbreviation: PCAPBA),N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine(abbreviation: 2PCAPA), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(abbreviation: NPB or a-NPD),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), and4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB). A plurality of host materials may be used.

A delayed fluorescent (thermally activated delayed fluorescent) compoundcan be also used as a host material.

In such a case, it is also preferable that the emitting layer includethe dopant material and the delayed fluorescent host material.

In an exemplary arrangement of the exemplary embodiment, the emittinglayer preferably does not include a phosphorescent metal complex, andpreferably does not include a metal complex other than thephosphorescent metal complex.

Emission Wavelength of Organic EL Device

When the organic EL device according to the exemplary embodiment isdriven, a main peak wavelength of light radiated from the organic ELdevice is preferably in a range from 380 nm to 500 nm, more preferablyin a range from 430 nm to 470 nm.

The main peak wavelength of light radiated from the organic EL device ismeasured as follows. Voltage is applied on the organic EL devices suchthat a current density becomes 10 mA/cm², where spectral radiancespectrum is measured by a spectroradiometer CS-2000 (manufactured byKonica Minolta, Inc.). A peak wavelength of an emission spectrum, atwhich the luminous intensity of the resultant spectral radiance spectrumis at the maximum, is measured and defined as the main peak wavelength(unit: nm).

Content Ratios of Dopant and Host Materials in Emitting Layer

When the emitting layer includes dopant and host materials, the contentratios of the dopant and host materials in the emitting layer preferablyfall within, for example, the following ranges.

The content ratio of the host material is preferably in a range from 80mass % to 99 mass %, more preferably in a range from 90 mass % to 99mass %, and further preferably in a range from 95 mass % to 99 mass %.

The content ratio of the dopant material is preferably in a range from 1mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass%, and further preferably in a range from 1 mass % to 5 mass %.

The upper limit of the total of the content ratios of the dopant andhost materials in the emitting layer is 100 mass %.

In particular, in a case of a blue fluorescent device, anthracenecompounds described below are preferably used as the host material.

Electron Transporting Layer

The electron transporting layer is a layer including a material havinghigh electron transportability (electron transporting material) and isinterposed between the emitting layer and the cathode or, when anelectron injecting layer is present, between the electron injectinglayer and the emitting layer.

The electron transporting layer may have a single-layer structure or amultilayer structure. For example, the electron transporting layer mayhave a two-layer structure including a first electron transporting layer(anode side) and a second electron transporting layer (cathode side). Inan exemplary arrangement of the exemplary embodiment, the electrontransporting layer having a single-layer structure is preferablyarranged adjacent to the emitting layer, and one of the electrontransporting layers included in the multilayer structure closest to theanode, that is, for example, the first electron transporting layerincluded in the above two-layer structure, is preferably arrangedadjacent to the emitting layer. In another exemplary arrangement of theexemplary embodiment, for example, the hole blocking layer describedbelow may be interposed between the electron transporting layer having asingle-layer structure and the emitting layer or between one of theelectron transporting layers included in the multilayer structureclosest to the emitting layer and the emitting layer.

Suitable Example in which First Compound is Used

The first compound (the compound according to the first exemplaryembodiment) is used as a material for the electron transporting zone,preferably used as a material for the electron injecting layer, theelectron transporting layer, the hole blocking layer, or the excitonblocking layer, more preferably used as a material for the electroninjecting layer or the electron transporting layer, and furtherpreferably used as a material for the electron transporting layer.

In the above-described electron transporting layer having a two-layerstructure, the first compound may be included in one of the first andsecond electron transporting layers and may be included in both firstand second electron transporting layers. In an example of the fifthexemplary embodiment, the first compound is preferably included in onlythe first electron transporting layer. In another example, the firstcompound is preferably included in only the second electron transportinglayer. In still another example, the first compound is preferablyincluded in both first and second electron transporting layers.

The second compound (the second compound that is an enantiomer of thefirst compound) and the mixture according to the second exemplaryembodiment can be also suitably used as a material for the electrontransporting zone.

Examples of the case where the second compound is used as a material forthe electron transporting zone include that described in “SuitableExample in Which First Compound Is Used” above in which “first compound”is replaced with “second compound”.

Examples of the case where the mixture according to the second exemplaryembodiment is used as a material for the electron transporting zoneinclude that described in “Suitable Example in Which First Compound IsUsed” above in which “first compound” is replaced with “mixtureaccording to the second exemplary embodiment”.

In an example of the fifth exemplary embodiment, the first compoundincluded in the organic EL device may include at least one deuteriumatom. Or, the first compound may be a mixture of the first compound inwhich all the hydrogen atoms are protium atoms (hereinafter, referred toas “protium isotope”) and the first compound in which at least one ofall the hydrogen atoms is a deuterium atom (deuterium isotope). Theprotium isotope may include deuterium atoms at a ratio equal to or lessthan the natural abundance ratio.

In an example of the fifth exemplary embodiment, the first compoundincluded in the electron injecting layer, the electron transportinglayer (including the first electron transporting layer, the secondelectron transporting layer, and the like), the hole blocking layer, andthe exciton blocking layer is preferably a protium isotope inconsideration of the production costs.

When the organic EL device includes the second compound, the secondcompound may include at least one deuterium atom. In such a case, thesecond compound may be a mixture of a protium isotope and a deuteriumisotope.

When the organic EL device includes the mixture according to the secondexemplary embodiment, at least one of the first compound or secondcompound included in the mixture may include at least one deuteriumatom. In such a case, in the mixture according to the second exemplaryembodiment, the first compound may be a mixture of a protium isotope anda deuterium isotope, the second compound may be a mixture of a protiumisotope and a deuterium isotope, and both first and second compounds maybe a mixture of a protium isotope and a deuterium isotope.

Thus, the organic EL device according to the fifth exemplary embodimentmay be an organic EL device in which at least one layer selected fromthe electron injecting layer, the electron transporting layer, the holeblocking layer, and the exciton blocking layer includes the firstcompound, second compound, or mixture according to the second exemplaryembodiment which is substantially composed only of a protium isotope.The expression “the first compound substantially composed only of aprotium isotope” means that the ratio of the content of a protiumisotope to the total amount of the first compound is 90 mol % or more,preferably 95 mol % or more, and more preferably 99 mol % or more (eachincluding 100%). The same applies to the expression “the second compoundsubstantially composed only of a protium isotope”. The expression “themixture according to the second exemplary embodiment which issubstantially composed only of a protium isotope” means that the ratioof the content of a protium isotope to the total amount of the first andsecond compounds is 90 mol % or more, preferably 95 mol % or more, andmore preferably 99 mol % or more (each including 100%).

Examples of a material for the electron transporting layer other thanthe first compound, the second compound, or the mixture according to thesecond exemplary embodiment include:

(1) a metal complex such as an aluminum complex, beryllium complex, andzinc complex,

(2) a hetero aromatic compound such as imidazole derivative,benzimidazole derivative, azine derivative, carbazole derivative, andphenanthroline derivative, and

(3) a high-molecular compound.

Examples of the metal complex include tris(8-quinolinolato)aluminum(III)(abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III)(abbreviation: Almq₃), bis(10-hydroxybenzo[h]quinolinato)beryllium(II)(abbreviation: BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

Examples of the heteroaromatic compound include2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene(abbreviation: OXD-7),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen),bathocuproine (abbreviation: BCP), and4,4′-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs).

Examples of the high-molecular compound includepoly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)](abbreviation: PF-Py) andpoly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)](abbreviation: PF-BPy).

The above materials have an electron mobility of 10⁻⁶ cm²/(V·s) or more.A material other than the above materials may be used for the electrontransporting layer as long as the material exhibits a higher electrontransportability than the hole transportability.

Electron Injecting Layer

The electron injecting layer is a layer including a material having highelectron injectability. Examples of the material for the electroninjecting layer include: an alkali metal such as lithium (Li) and cesium(Cs); an alkaline-earth metal such as magnesium (Mg), calcium (Ca), andstrontium (Sr); a rare-earth metal such as europium (Eu) and ytterbium(Yb); and a compound including any of the above metals. Examples of sucha compound include an alkali metal oxide, an alkali metal halide, analkali metal-containing organic complex, an alkaline-earth metal oxide,an alkaline-earth metal halide, an alkaline-earth metal-containingorganic complex, a rare-earth metal oxide, a rare-earth metal halide,and a rare-earth metal-containing organic complex. A plurality of theabove compounds may be used in a mixture.

In addition, the alkali metal, alkaline earth metal or the compoundthereof may be added to the material exhibiting the electrontransportability in use. Specifically, for instance, magnesium (Mg)added to Alq may be used. In this case, the electrons can be moreefficiently injected from the anode.

Alternatively, the electron injecting layer may be provided by acomposite material in a form of a mixture of the organic compound andthe electron donor. Such a composite material exhibits excellentelectron injectability and electron transportability since the organiccompound receives electrons from the electron donor. In this case, theorganic compound is preferably a material excellent in transporting thereceived electrons. Specifically, the above examples (e.g., the metalcomplex and the hetero aromatic compound) of the material forming theelectron transporting layer are usable. As the electron donor, anymaterial exhibiting electron donating property to the organic compoundis usable. Specifically, the electron donor is preferably alkali metal,alkaline earth metal and rare earth metal such as lithium, cesium,magnesium, calcium, erbium and ytterbium. The electron donor is alsopreferably alkali metal oxide and alkaline earth metal oxide such aslithium oxide, calcium oxide, and barium oxide. Moreover, a Lewis basesuch as magnesium oxide is usable. Further, the organic compound such astetrathiafulvalene (abbreviation: TTF) is usable.

Cathode

It is preferable to use metal, an alloy, an electroconductive compound,and a mixture thereof, which have a small work function (specifically,3.8 eV or less) for the cathode. Examples of the material for thecathode include elements belonging to Groups 1 and 2 in the periodictable of the elements, specifically, the alkali metal such as lithium(Li) and cesium (Cs), the alkaline earth metal such as magnesium (Mg),calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) includingthe alkali metal or the alkaline earth metal, the rare earth metal suchas europium (Eu) and ytterbium (Yb), and alloys including the rare earthmetal.

It should be noted that the vacuum deposition method and the sputteringmethod are usable for forming the cathode using the alkali metal,alkaline earth metal and the alloy thereof. Further, when a silver pasteis used for the cathode, the coating method and the inkjet method areusable.

By providing the electron injecting layer, various conductive materialssuch as Al, Ag, ITO, graphene, and indium oxide-tin oxide containingsilicon or silicon oxide may be used for forming the cathode regardlessof the work function. The conductive materials can be formed into a filmusing the sputtering method, inkjet method, spin coating method and thelike.

Insulation Layer

In an organic EL device, pixel defects are likely to occur due toleakage or short circuiting because an electric field is applied toultrathin films. In order to prevent this, an insulation layer that isan insulative thin film layer may be interposed between a pair of theelectrodes.

Examples of the material for the insulation layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, andvanadium oxide. A mixture or laminate including any of the abovematerials may be also used.

Space Layer

The space layer is, for example, a layer interposed between afluorescent emitting layer and a phosphorescent emitting layer in a casewhere the fluorescent emitting layer and the phosphorescent emittinglayer are stacked on top of each other, in order to prevent the excitonsgenerated in the phosphorescent emitting layer from being diffused intothe fluorescent emitting layer or to adjust carrier balance. The spacelayer may be also interposed between a plurality of phosphorescentemitting layers.

Since the space layer is interposed between the emitting layers, amaterial for the space layer preferably has both electrontransportability and hole transportability. Further, in order to preventthe diffusion of the triplet energy into adjacent phosphorescentemitting layers, the triplet energy is preferably 2.6 eV or more.Examples of the material that can be used for forming the space layerare the same as the above-described examples of the material that can beused for forming the hole transporting layer.

Blocking Layer

Blocking layers, such as an electron blocking layer, a hole blockinglayer, and an exciton blocking layer, may be arranged adjacent to theemitting layer. The electron blocking layer is a layer that preventselectrons from leaking from the emitting layer to the hole transportinglayer. The hole blocking layer is a layer that prevents holes fromleaking from the emitting layer to the electron transporting layer. Theexciton blocking layer prevents the excitons generated in the emittinglayer from being diffused into neighboring layers and confines theexcitons in the emitting layer.

Each layer included in the organic EL device can be formed by a knownmethod, such as vapor deposition or a coating method. The vapordeposition is exemplified by vacuum deposition and molecular beamepitaxy (MBE)). The coating method is exemplified by a method using asolution of a compound that forms a layer, such as dipping, spincoating, casting, bar coating, and roll coating.

The thickness of each layer is not particularly limited. The thicknessis preferably in a range from 5 nm to 10 μm and more preferably in arange from 10 nm to 0.2 μm, because excessively small film thickness islikely to cause defects (e.g. pin holes) and excessively large thicknessleads to the necessity of applying high voltage and consequent reductionin efficiency.

According to the fifth exemplary embodiment, an organicelectroluminescence device that includes a compound capable of enhancingthe performance of the organic EL device and, in particular, a compoundcapable of reducing the drive voltage of the organic EL device can beprovided.

Sixth Exemplary Embodiment Electronic Device

An electronic device according to a sixth exemplary embodiment includesany of the organic EL devices according to the above-described exemplaryembodiment. Examples of the electronic device include a display deviceand a light-emitting unit. Examples of the display device include adisplay component (e.g., an organic EL panel module), TV, mobile phone,tablet and personal computer. Examples of the light-emitting unitinclude an illuminator and a vehicle light.

According to the sixth exemplary embodiment, an electronic deviceincluding an organic electroluminescence device that includes a compoundcapable of enhancing the performance of the organic EL device and, inparticular, a compound capable of reducing the drive voltage of theorganic EL device can be provided.

The organic EL device can be used in an electronic device, such as adisplay component (e.g., an organic EL panel module), a display of atelevision, mobile phone, personal computer, or the like, or alight-emitting unit (e.g., a illuminator and a vehicle light).

EXAMPLES

Examples according to the invention are described below. The inventionis not limited to Examples below.

Compounds

The compounds represented by the formula (1) which were used in Examples1 to 8 are described below.

In Example 1, a mixture (isomer mixture) of compounds ET-1a and ET-1 bwas used.

In the following description of Examples, the mixture of the compoundsET-1a and ET-1b is referred to collectively as “ET-1”.

In Example 2, a mixture of compounds ET-2a and ET-2b (isomer mixture:referred to collectively as ET-2) was used. In Example 3, a mixture ofcompounds ET-3a and ET-3b (isomer mixture: referred to collectively asET-3) was used. In Example 4, a mixture of the compounds ET-4a and ET-4b(isomer mixture: referred to collectively as ET-4) was used. In Example5, a mixture of compounds ET-5a and ET-5b (isomer mixture: referred tocollectively as ET-5) was used. In Example 6, a mixture of compoundsET-6a and ET-6b (isomer mixture: referred to collectively as ET-6) wasused. In Example 7, a mixture of compounds ET-8a and ET-8b (isomermixture: referred to collectively as ET-8) was used. In Example 8, amixture of compounds ET-9a and ET-9b (isomer mixture: referred tocollectively as ET-9) was used. In Synthesis Example 7, a mixture ofcompounds ET-7a and ET-7b was synthesized.

The structure of the compound used for producing an organic EL device ofComparative Example 1 is described below.

The structures of the other compounds used for producing organic ELdevices of Examples 1 to 8 and Comparative Example 1 are describedbelow.

Preparation of Organic EL Devices

Organic EL devices were prepared and evaluated as described below.

Example 1

A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured byGeomatec Co., Ltd.) having an ITO transparent electrode (anode) wasultrasonic-cleaned in isopropyl alcohol for five minutes, and thenUV-ozone-cleaned for 30 minutes. The film thickness of ITO was 130 nm.

After the glass substrate having the transparent electrode line wascleaned, the glass substrate was mounted on a substrate holder of avacuum evaporation apparatus. Firstly, a compound HT-1 and a compoundHI-1 were co-deposited on a surface of the glass substrate where thetransparent electrode line was provided in a manner to cover thetransparent electrode, thereby forming a 10-nm-thick hole injectinglayer. The concentrations of the compound HT-1 and the compound HI-1 inthe hole injecting layer were 97 mass % and 3 mass %, respectively.

Next, the compound HT-1 was vapor-deposited on the hole injecting layerto form an 80-nm-thick first hole transporting layer.

A compound EBL-1 was vapor-deposited on the first hole transportinglayer to form a 5-nm-thick second hole transporting layer.

Next, a compound BH-1(host material) and a compound BD-1(dopantmaterial) were co-deposited on the second hole transporting layer toform a 25-nm-thick emitting layer. The concentrations of the compoundBH-1 and the compound BD-1 in the emitting layer were 96 mass % and 4mass %, respectively.

Next, a compound HBL-1 was vapor-deposited on the emitting layer to forma 5-nm-thick first electron transporting layer.

The compound ET-1 and a compound Liq were co-deposited on the firstelectron transporting layer to form a 20-nm-thick second electrontransporting layer. The ratios of the compound ET-1 and the compound Liqin the second electron transporting layer were both 50 mass %. It shouldbe noted that Liq is an abbreviation for (8-quinolinolato)lithium.

Yb was vapor-deposited on the second electron transporting layer to forma 1-nm-thick electron injecting layer.

Metal Al was vapor-deposited on the electron injecting layer to form a50-nm-thick cathode.

A device arrangement of the organic EL device in Example 1 is roughlyshown as follows.

ITO(130)/HT-1:HI-1(10, 970/03%)/HT-1(80)/EBL-1(5)/BH-1:BD-1(25,96%:4%)/HBL-1(5)/ET-1:Liq(20, 50%:50%)/Yb(1)/Al (50)

The numerals in parentheses represent a film thickness (unit: nm).

The numerals (97%:3%) represented by percentage in the same parenthesesindicate a ratio (mass %) between the compound HT-1 and the compoundHI-1 in the hole injecting layer, the numerals (96%:4%) represented bypercentage in the same parentheses indicate a ratio (mass %) between thecompound BH-1 and the compound BD-1 in the emitting layer, and thenumerals (50%:50%) represented by percentage in the same parenthesesindicate a ratio (mass %) between the compound ET-1 and the compound Liqin the second electron transporting layer.

Examples 2 to 8

Organic EL devices of Examples 2 to 8 were each prepared as in Example1, except that a corresponding one of the compounds described in Table 1was used instead of the compound ET-1 included in the second electrontransporting layer in Example 1.

Comparative Example 1

An organic EL device of Comparative Example 1 was prepared as in Example1, except that the compound described in Table 1 was used instead of thecompound ET-1 included in the second electron transporting layer inExample 1.

Evaluation of Organic EL Devices

The organic EL devices prepared in Examples 1 to 8 and ComparativeExample 1 were subjected to the following evaluation. Note that,although a compound Ref-1 used in Comparative Example 1 is not thecompound represented by the formula (1), the compound Ref-1 is describedin the same column as “Compound represented by Formula (1)” of Example 1for the sake of simplicity.

Drive Voltage

The initial property of each of the organic EL devices was measuredwhile it was driven at room temperature (25° C.) and a DC (directcurrent) constant-current of 50 mA/cm² in order to measure voltage(unit: V). Table 1 lists the results.

TABLE 1 Second electron transporting layer First electron CompoundVoltage transporting represented by [V] @50 Emitting layer layer Formula(1) mA/cm² Example 1 BH-1 BD-1 HBL-1 ET-1 4.65 Example 2 BH-1 BD-1 HBL-1ET-2 4.66 Example 3 BH-1 BD-1 HBL-1 ET-3 4.68 Example 4 BH-1 BD-1 HBL-1ET-4 4.65 Example 5 BH-1 BD-1 HBL-1 ET-5 4.54 Example 6 BH-1 BD-1 HBL-1ET-6 4.56 Example 7 BH-1 BD-1 HBL-1 ET-8 4.54 Example 8 BH-1 BD-1 HBL-1ET-9 4.65 Comparative BH-1 BD-1 HBL-1 Ref-1 5.00 Example 1

In Examples 1 to 8, where the compound represented by the formula (1)was included in the second electron transporting layer, the drivevoltage was reduced compared with Comparative Example 1, where thecompound represented by the formula (1) was replaced with the compoundRef-1.

Synthesis of Compounds Synthesis Example 1 (Synthesis of Compound ET-1)

A raw material (the compound M-1: isomer mixture) (4.4 g),2-chloro-4,6-diphenyl-1,3,5-triazine (5.12 g), Pd(PPh₃)₄ (0.603 g), 87mL of dioxane, and 22 mL of a 2M aqueous solution of potassium phosphatewere charged into a flask. Then, purging was performed with an argongas. Subsequently, stirring was performed for 7 hours while heating wasperformed at 80° C. After the temperature had been reduced to roomtemperature (25° C.), methanol was added to the resulting reactionsolution. The precipitated solid was collected by filtration and thenpurified by silica gel chromatography. The resulting crude product wascleaned with toluene. Hereby, 1.87 g of the compound ET-1 was prepared(yield: 30%). The results of mass spectroscopy confirmed that m/e=717and this compound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-1 was a mixture of ET-1aand ET-1b. Note that, in the reaction formula described in SynthesisExample 1, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-1a is described as a representative of “compound ET-1”.

Synthesis Example 2 (Synthesis of Compound ET-2)

ET-2 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine(4.5 g) under the same conditions as those described in SynthesisExample 1 as a white solid (2.0 g, yield: 39%).

The results of mass spectroscopy confirmed that m/e=869 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1 b), ET-2 was a mixture of ET-2aand ET-2b. Note that, in the reaction formula described in SynthesisExample 2, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-2a is described as a representative of “compound ET-2”.

Synthesis Example 3 (Synthesis of Compound ET-3)

ET-3 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and 2-([1,1′-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine(4.5 g) under the same conditions as those described in SynthesisExample 1 as a white solid (1.9 g, yield: 36%).

The results of mass spectroscopy confirmed that m/e=869 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-3 was a mixture of ET-3aand ET-3b. Note that, in the reaction formula described in SynthesisExample 3, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-3a is described as a representative of “compound ET-3”.

Synthesis Example 4 (Synthesis of Compound ET-4)

ET-4 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.5 g) underthe same conditions as those described in Synthesis Example 1 as a whitesolid (1.3 g, yield: 26%).

The results of mass spectroscopy confirmed that m/e=869 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-4 was a mixture of ET-4aand ET-4b. Note that, in the reaction formula described in SynthesisExample 4, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-4a is described as a representative of “compound ET-4”.

Synthesis Example 5 (Synthesis of Compound ET-5)

ET-5 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and 4-chloro-2,6-diphenylpyrimidine (3.5 g) under the sameconditions as those described in Synthesis Example 1 as a white solid(1.8 g, yield: 42%).

The results of mass spectroscopy confirmed that m/e=715 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-5 was a mixture of ET-5aand ET-5b. Note that, in the reaction formula described in SynthesisExample 5, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-5a is described as a representative of “compound ET-5”.

Synthesis Example 6 (Synthesis of Compound ET-6)

ET-6 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (4.5 g)under the same conditions as those described in Synthesis Example 1 as awhite solid (2.6 g, yield: 51%).

The results of mass spectroscopy confirmed that m/e=867 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-6 was a mixture of ET-6aand ET-6b. Note that, in the reaction formula described in SynthesisExample 6, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-6a is described as a representative of “compound ET-6”.

Synthesis Example 7 (Synthesis of Compound ET-7)

ET-7 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and 4-([1,1′-biphenyl]-3-yl)-6-chloro-2-phenylpyrimidine (4.5 g)under the same conditions as those described in Synthesis Example 1 as awhite solid (1.6 g, yield: 32%).

The results of mass spectroscopy confirmed that m/e=867 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-7 was a mixture of ET-7aand ET-7b. Note that, in the reaction formula described in SynthesisExample 7, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-7a is described as a representative of “compound ET-7”.

Synthesis Example 8 (Synthesis of Compound ET-8)

ET-8 was prepared using a raw material (compound M-1: isomer mixture)(3.0 g) and3′-(6-chloro-2-phenylpyrimidin-4-yl)-[1,1′-biphenyl]-4-carbonitrile (4.8g) under the same conditions as those described in Synthesis Example 1as a white solid (1.5 g, yield: 28%).

The results of mass spectroscopy confirmed that m/e=917 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-8 was a mixture of ET-8aand ET-8b. Note that, in the reaction formula described in SynthesisExample 8, only the structure of the compound M-1a is described as arepresentative of “compound M-1”, and only the structure of the compoundET-8a is described as a representative of “compound ET-8”.

Synthesis Example 9 (Compound ET-9)

ET-9 was synthesized by the same synthesis scheme as in SynthesisExample 1, except that2-chloro-4,6-di(phenyl-2,3,4,5,6-d5)-1,3,5-triazine was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine.

The results of mass spectroscopy confirmed that m/e=736 and thiscompound was the target substance.

Since the starting material used (compound M-1) was an isomer mixture(mixture of the compounds M-1a and M-1b), ET-9 was a mixture of ET-9aand ET-9b. Note that, in the reaction formula described in SynthesisExample 9, only the structure of the compound ET-9a is described as arepresentative of “compound ET-9”.

Comparative Synthesis Example 1 (Synthesis of Compound Ref-1)

Into a flask, 2-chloro-4,6-diphenyl-1,3,5-triazine (3.01 g), thecompound M-2 (2.02 g), Pd(PPh₃)₄ (0.436 g), 76 mL of dioxane, and 9.4 mLof a 2M aqueous solution of sodium carbonate were charged. Then, purgingwas performed with an argon gas. Subsequently, heating and stirring wereperformed for 8 hours while refluxing was performed. After thetemperature had been reduced to room temperature (25° C.), the resultingsolution was concentrated. Subsequently, methanol was added to thesolution. The precipitated solid was collected by filtration and thenpurified by silica gel chromatography. The resulting crude product wasrecrystallized using toluene. Hereby, 2.86 g of a compound Ref-1 wasprepared (yield: 78%). The results of mass spectroscopy confirmed thatm/e=486 and this compound was the target substance.

What is claimed is:
 1. A compound represented by a formula (1) below,

in the formula (1), X¹ to X⁵ each independently represent a nitrogenatom or CR¹⁰, two or more of X¹ to X⁵ are each a nitrogen atom, at leastone combination of adjacent two or more of a plurality of R¹⁰ are bondedto each other to form a substituted or unsubstituted monocyclic ring,are bonded to each other to form a substituted or unsubstituted fusedring, or are not bonded to each other, Y¹ to Y⁵ each independentlyrepresent a nitrogen atom or CR²⁰, one or more of Y¹ to Y⁵ are each anitrogen atom, at least one combination of adjacent two or more of aplurality of R²⁰ are bonded to each other to form a substituted orunsubstituted monocyclic ring, are bonded to each other to form asubstituted or unsubstituted fused ring, or are not bonded to eachother, at least one combination of adjacent two or more of a pluralityof R⁵ are bonded to each other to form a substituted or unsubstitutedmonocyclic ring, are bonded to each other to form a substituted orunsubstituted fused ring, or are not bonded to each other, at least onecombination of adjacent two or more of a plurality of R⁶ are bonded toeach other to form a substituted or unsubstituted monocyclic ring, arebonded to each other to form a substituted or unsubstituted fused ring,or are not bonded to each other, at least one combination of adjacenttwo or more of a plurality of R⁷ are bonded to each other to form asubstituted or unsubstituted monocyclic ring, are bonded to each otherto form a substituted or unsubstituted fused ring, or are not bonded toeach other, R¹⁰, R²⁰, and R⁵ to R⁷ forming neither the substituted orunsubstituted monocyclic ring nor the substituted or unsubstituted fusedring, and R⁸ and R⁹ each independently represent a hydrogen atom, ahalogen atom, a cyano group, a nitro group, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkenyl group having 2 to 50 carbon atoms, a substitutedor unsubstituted alkynyl group having 2 to 50 carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 50 ring carbonatoms, a group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a group representedby —O—(R₉₀₄), a group represented by —S—(R₉₀₅), a group represented by—N(R₉₀₆)(R₉₀₇), a substituted or unsubstituted aryl group having 6 to 50ring carbon atoms, or a substituted or unsubstituted heterocyclic grouphaving 5 to 50 ring atoms, when a plurality of R¹⁰ are present, theplurality of R¹⁰ are mutually the same or different, when a plurality ofR²⁰ are present, the plurality of R²⁰ are mutually the same ordifferent, the plurality of R⁵ are mutually the same or different, theplurality of R⁶ are mutually the same or different, the plurality of R⁷are mutually the same or different, a represents 0, 1, 2, or 3, when ais 2 or 3, a plurality of L1 are mutually the same or different, brepresents 0, 1, 2, or 3, when b is 2 or 3, a plurality of L2 aremutually the same or different, when a and b are each independently 1,2, or 3, L1 and L2 each independently represent a single bond, asubstituted or unsubstituted arylene group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted divalent heterocyclic grouphaving 5 to 50 ring atoms, when only one of Y¹ to Y⁵ is a nitrogen atom,L2 is not a single bond, or any of Y¹ to Y⁵ other than a nitrogen atomis not CH, in the compound represented by the formula (1), R₉₀₁ to R₉₀₇each independently represent a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, asubstituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to50 ring atoms, when two or more R₉₀₁ are present, the two or more R₉₀₁are mutually the same or different, when two or more R₉₀₂ are present,the two or more R₉₀₂ are mutually the same or different, when two ormore R₉₀₃ are present, the two or more R₉₀₃ are mutually the same ordifferent, when two or more R₉₀₄ are present, the two or more R₉₀₄ aremutually the same or different, when two or more R₉₀₅ are present, thetwo or more R₉₀₅ are mutually the same or different, when two or moreR₉₀₆ are present, the two or more R₉₀₆ are mutually the same ordifferent, and when two or more R₉₀₇ are present, the two or more R₉₀₇are mutually the same or different.
 2. The compound according to claim1, wherein at least one combination of adjacent two or more of theplurality of R¹⁰ are not bonded to each other, at least one combinationof adjacent two or more of the plurality of R²⁰ are not bonded to eachother, at least one combination of adjacent two or more of the pluralityof R⁵ are not bonded to each other, at least one combination of adjacenttwo or more of the plurality of R⁶ are not bonded to each other, and atleast one combination of adjacent two or more of the plurality of R⁷ arenot bonded to each other.
 3. The compound according to claim 1, whereinin the formula (1), among partial structures represented by formulae(1A), (1B), and (1C) below, the partial structures represented by theformulae (1A) and (1B) are different from each other,

in the formula (1C), R⁵ to R⁹ each independently represent the same asR⁵ to R⁹ in the formula (1), in the formula (1A), X¹ to X⁵, L1, and aeach independently represent the same as X¹ to X⁵, L1, and a in theformula (1), and * represents a bonding position to *1 in the partialstructure represented by the formula (1C) in the formula (1), and in theformula (1B), Y¹ to Y⁵, L2, and b each independently represent the sameas Y¹ to Y⁵, L2, and b in the formula (1), and * represents a bondingposition to *2 in the partial structure represented by the formula (1C)in the formula (1).
 4. The compound according to claim 1, wherein in theformula (1), partial structures represented by formulae (1A) and (1B)below are the same as each other,

in the formula (1C), R⁵ to R⁹ each independently represent the same asR⁵ to R⁹ in the formula (1), in the formula (1A), X¹ to X⁵, L1, and aeach independently represent the same as X¹ to X⁵, L1, and a in theformula (1), and * represents a bonding position to *1 in the partialstructure represented by the formula (1C) in the formula (1), and in theformula (1B), Y¹ to Y⁵, L2, and b each independently represent the sameas Y¹ to Y⁵, L2, and b in the formula (1), and * represents a bondingposition to *2 in the partial structure represented by the formula (1C)in the formula (1).
 5. The compound according to claim 3, wherein in theformula (1A), two or three of X¹ to X⁵ are each a nitrogen atom, and inthe formula (1B), one, two, or three of Y¹ to Y⁵ are each a nitrogenatom.
 6. The compound according to claim 3, wherein the partialstructure represented by the formula (1A) is represented by any offormulae (1A-1) to (1A-3) below, and the partial structure representedby the formula (1B) is represented by any of formulae (1B-1) to (1B-6)below,

in the formulae (1A-1) to (1A-3), L1 and a each independently representthe same as L1 and a in the formula (1), and R¹¹, R¹², R¹³, and R¹⁴ eachindependently represent the same as R¹⁰ in the formula (1),

in the formulae (1B-1) to (1B-6), L2 and b each independently representthe same as L2 and b in the formula (1), and R²¹ to R²⁵ eachindependently represent the same as R²⁰ in the formula (1).
 7. Thecompound according to claim 6, wherein when the partial structurerepresented by the formula (1A) is represented by the formula (1A-1),the partial structure represented by the formula (1B) is represented bythe formula (1B-1), when the partial structure represented by theformula (1A) is represented by the formula (1A-2), the partial structurerepresented by the formula (1B) is represented by the formula (1B-2),and when the partial structure represented by the formula (1A) isrepresented by the formula (1A-3), the partial structure represented bythe formula (1B) is represented by the formula (1B-4).
 8. The compoundaccording to claim 1, wherein the compound represented by the formula(1) is a compound represented by a formula (10) below,

in the formula (10), X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, and beach independently represent the same as X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ toR⁹, L1, L2, a, and b in the formula (1), and R¹² and R¹⁴ eachindependently represent the same as R¹⁰ in the formula (1), and R²² andR²⁴ each independently represent the same as R²⁰ in the formula (1). 9.The compound according to claim 1, wherein the compound represented bythe formula (1) is a compound represented by a formula (10-1a) below oran enantiomer of the compound represented by the formula (10-1a),

in the formula (10-1a), X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ to R⁹, L1, L2, a, andb each independently represent the same as X¹, X³, X⁵, Y¹, Y³, Y⁵, R⁵ toR⁹, L1, L2, a, and b in the formula (1), and R¹² and R¹⁴ eachindependently represent the same as R¹⁰ in the formula (1), and R²² andR²⁴ each independently represent the same as R²⁰ in the formula (1). 10.The compound according to claim 1, wherein L1 and L2 each independentlyrepresent a single bond, a substituted or unsubstituted arylene grouphaving 6 to 30 ring carbon atoms, or a substituted or unsubstituteddivalent heterocyclic group having 5 to 30 ring atoms.
 11. The compoundaccording to claim 1, wherein L1 and L2 each independently represent asingle bond, a substituted or unsubstituted phenylene group, asubstituted or unsubstituted biphenylene group, a substituted orunsubstituted terphenylene group, a substituted or unsubstitutednaphthylene group, a substituted or unsubstituted phenanthrylene group,a substituted or unsubstituted fluorenylene group, a substituted orunsubstituted dibenzofuranylene group, a substituted or unsubstituteddibenzothienylene group, a substituted or unsubstituted pyridylenegroup, or a substituted or unsubstituted quinolylene group.
 12. Thecompound according to claim 1, wherein a is 0 or 1, and b is 0 or
 1. 13.The compound according to claim 1, wherein R¹⁰, R²⁰, and R⁵ to R⁹ eachindependently represent a hydrogen atom, a halogen atom, a cyano group,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, a group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a grouprepresented by —O—(R₉₀₄), a group represented by —N(R₉₀₆)(R₉₀₇), asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to30 ring atoms.
 14. The compound according to claim 1, wherein R¹⁰,R²⁰and R⁵ to R⁹ each independently represent a hydrogen atom, a halogenatom, a cyano group, a substituted or unsubstituted alkyl group having 1to 18 carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 18 ring carbon atoms, a substituted or unsubstituted arylgroup having 6 to 18 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 18 ring atoms.
 15. Thecompound according to claim 1, wherein R¹⁰, R²⁰, and R⁵ to R⁹ eachindependently represent a hydrogen atom, or a group represented by anyof formulae (A1) to (A31) below,

in the formulae (A1) to (A31), Z₁ represents an oxygen atom, a sulfuratom, or NRb₃, at least one combination of adjacent two or more of aplurality of Ra are bonded to each other to form a substituted orunsubstituted monocyclic ring, are bonded to each other to form asubstituted or unsubstituted fused ring, or are not bonded to eachother, a pair of Rb₁ and Rb₂ are bonded to each other to form asubstituted or unsubstituted monocyclic ring, are bonded to each otherto form a substituted or unsubstituted fused ring, or are not bonded toeach other, Rb₁ and Rb₂ forming neither the substituted or unsubstitutedmonocyclic ring nor the substituted or unsubstituted fused ring, and Rb₃each independently represent a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to30 ring atoms, Ra forming neither the substituted or unsubstitutedmonocyclic ring nor the substituted or unsubstituted fused ring eachindependently represent a hydrogen atom, a halogen atom, a cyano group,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms, a group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃), a grouprepresented by —O—(R₉₀₄), a group represented by —N(R₉₀₆)(R₉₀₇), asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heterocyclic group having 5 to30 ring atoms, R₉₀₁ to R₉₀₄, R₉₀₆, and R₉₀₇ each independently representthe same as R₉₀₁ to R₉₀₄, R₉₀₆, and R₉₀₇ in the formula (1), a pluralityof Ra are mutually the same or different, when a plurality of Z₁ arepresent, the plurality of Z₁ are mutually the same or different, when aplurality of Rb₁ are present, the plurality of Rb₁ are mutually the sameor different, when a plurality of Rb₂ are present, the plurality of Rb₂are mutually the same or different, and when a plurality of Rb₃ arepresent, the plurality of Rb₃ are mutually the same or different. 16.The compound according to claim 1, wherein R⁵ to R⁹ each represent ahydrogen atom, and R¹⁰ and R²⁰ each independently represent a hydrogenatom, a halogen atom, a cyano group, a substituted or unsubstitutedalkyl group having 1 to 18 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 18 ring carbon atoms, a substituted orunsubstituted aryl group having 6 to 18 ring carbon atoms, or asubstituted or unsubstituted heterocyclic group having 5 to 18 ringatoms.
 17. A mixture comprising: the compound according to claim 1 as afirst compound; and a second compound that is an enantiomer of the firstcompound.
 18. A material for organic electroluminescence devicecomprising the compound according to claim
 1. 19. A material for organicelectroluminescence device comprising the mixture according to claim 17.20. An organic electroluminescence device comprising: a cathode; ananode; and one or more organic layers interposed between the cathode andthe anode, wherein at least one of the organic layers comprises thecompound according to claim 1 as a first compound.
 21. The organicelectroluminescence device according to claim 20, wherein the organiclayers comprise: an emitting layer interposed between the cathode andthe anode; and an electron transporting layer interposed between thecathode and the emitting layer, and the electron transporting layercomprises the first compound.
 22. The organic electroluminescence deviceaccording to claim 21 wherein, the electron transporting layercomprises: a first electron transporting layer interposed between thecathode and the emitting layer, and a second electron transporting layerinterposed between the first electron transporting layer and thecathode, and the second electron transporting layer comprises the firstcompound.
 23. The organic electroluminescence device according to claim21, wherein the organic layers comprise a hole transporting layerinterposed between the anode and the emitting layer.
 24. The organicelectroluminescence device according to claim 20, wherein at least oneof the organic layers comprises the first compound and a second compoundthat is an enantiomer of the first compound.
 25. An electronic devicecomprising the organic electroluminescence device according to claim 20.26. The compound according to claim 4, wherein in the formula (1A), twoor three of X¹ to X⁵ are each a nitrogen atom, and in the formula (1B),two or three of Y¹ to Y⁵ are each a nitrogen atom.
 27. The compoundaccording to claim 4, wherein when the partial structure represented bythe formula (1A) is represented by a formula (1A-1) below, the partialstructure represented by the formula (1B) is represented by a formula(1B-1) below, when the partial structure represented by the formula (1A)is represented by a formula (1A-2) below, the partial structurerepresented by the formula (1B) is represented by a formula (1B-2)below; and when the partial structure represented by the formula (1A) isrepresented by a formula (1A-3) below, the partial structure representedby the formula (1B) is represented by a formula (1B-4) below,

in the formulae (1A-1) to (1A-3), L1 and a each independently representthe same as L1 and a in the formula (1), and R¹¹, R¹², R¹³, and R¹⁴ eachindependently represent the same as R¹⁰ in the formula (1), in theformulae (1B-1), (1B-2), and (1B-4), L2 and b each independentlyrepresent the same as L2 and b in the formula (1), and R²² to R²⁵ eachindependently represent the same as R²⁰ in the formula (1).